The history of Chatham goes way beyond the year it was incorporated (1712, in case you were wondering) with its landscape and salt ponds being created by glacial action during the last Ice Age, creating the beauty you will be exploring during your Cape Cod journey. Offering historical sites, tranquil beaches, and the world-famous Chatham Lighthouse, the time you spend in this town will only get better when you choose Pretty Picky Properties for your vacation accommodations. Reflecting the beauty and charm of Chatham, our homes and cottages will welcome every travelers, creating a safe space filled with all the comforts of home. This guide to things to do in Chatham will show you more about the town and about all you can expect from our Chatham escapes.
Something for Everyone
The appeal of our New England town reaches out to everyone who steps within its city limits, and crossing boundaries that you might not expect from a vacation destination. History is all around as you pose for family pictures at the base of the famous Chatham Lighthouse, constructed in the very early years of the 19th century (1808, to be exact) marvel at the Chatham Windmill, which was once used for grinding corn, and explore the nautical history of Cape Cod at the Chatham Marconi Maritime Center. But Chatham is also a movie making town, its land and seascape having been featured in several movies, including “The Finest Hours” a true story about a famous Coast Guard rescue. And then, on another front, there is the natural side of our Cape Cod hometown, offering warm water beaches, the Monomoy National Wildlife Refuge, and sunsets that will literally take away your ability to speak. A vacation spent in Chatham is destined to be a well rounded one and we’ve listed more of our favorite adventures in more detail in the next paragraphs.
Chatham Railroad Museum, 153 Depot Road, Closed Sundays and Mondays
Traveling by train used to be one of the few ways you could get to Cape Cod after the construction of the railway bridge, but it was more than just a way to get here, train travel was the source of romance and excitement. Today, we tend to drive or fly everywhere, but when you visit the Chatham Railroad Museum, you may find yourself longing for the romance of those long ago days. Housed in a former railway depot, the museum has long been a favored attraction, opening its doors in 1960, and the structure itself was placed on the National Register of Historic Places in 1978. Its impeccably restored 1910 caboose is probably our favorite exhibit of all, allowing visitors to step inside and see for themselves what the romance of train travel was all about.
Families Love Us
In addition to the Chatham Railroad Museum, there is a large amount of Chatham, Cape Cod things to do with families that will appeal to all age groups, activities which include, of course, toes in the sand time. There are many beaches in Chatham in which you can frolic in the surf and build sandcastles at water’s edge, but perhaps the best known one is Lighthouse Beach, lying in the shadow of, yes, you guessed it, the Chatham Lighthouse. It’s white sands are soft and stunning, framing deep blue waters perfectly, and when the sun is setting behind the Chatham Lighthouse, well, we dare you not to fall in love. We’ve listed more family friendly activities below.
AWSC Shark Center Chatham, 235 Orleans Road in North Chatham
Sharks have fascinated us for years and the AWSC Shark Center in Chatham will make your children excited about learning. Offering a selection of water tours that explore the world beneath the waters while educating travelers about sharks and their importance in the earth continuum.
Chatham Candy Manor, 484 Main Street in Chatham, Open Daily 10-6
Do not even try to tell us candy is just for kids, or if you really think that way, we invite you to walk inside the Chatham Candy Manor and spend a little time there. We’re pretty sure it won’t take long to change your mind forever as you scope out all the delicious treats found under its roof, including seasonal collections that offer fun treats such as candies that look like mummies, bats, and pumpkins at Halloween. Featuring small batch fudge that will melt your heart, hand dipped chocolates, truffles, creams, and caramels, and they even offer sugar free sweets that don’t taste sugar free at all.
Chatham Orpheum Theater, 637 Main Street in Chatham
Rainy days and lazy days are always the best times to see a movie and although you can choose to stream movies on our large televisions and stay comfy and cozy as the rain drums down on the roof overhead, the Chatham Orpheum Theater offers fun things to do in Chatham. Offering artsy films and special events, kid’s movies, and classic movies that you will thrill to see on the big screen. Also offering a concession stand that includes pizza, wings, sandwiches, and a host of ice cream treats, honestly, hanging out at the Orpheum is one of our favorite things to do any time of the year.
Cause for Celebration
Just like in your own hometown, the holidays are a time for celebration and the special events listed below celebrate many of the bigger holidays with local celebrations that offer an all-American small town charm and appeal.
4th of July Parade
While parades seem to be disappearing from the national landscape, the Chatham 4th of July Parade is an event we look forward to every year. Offering a different theme each year (in 2024 the theme was Chatham-It’s a Shore Thing!) there will be colorful floats, classic cars, fire trucks, and fishing boats and a vibe of cheer and happiness that will definitely make you feel proud to be an American.
Pumpkin People in the Park at Halloween
Also offering trick-or-treating and costume parties, the Pumpkin People in the Park event is not as spooky as it sounds and is a lot of fun! Chatham has been listed as America’s 4th best town for Halloween and the pumpkins that are made to look like people are one of the top reasons. Kate Gould Park is the “scene of the crime,” and the pumpkins are sure to make you laugh.
Christmas Stroll in Chatham
As you can imagine, Christmas on Cape Cod already looks like a scene straight off a Christmas card, but you may not be able to imagine it gets even better with the Christmas Stroll in Chatham. The shops on Main Street are decorated in colorful lights that shimmer against a blanket of snow that is on the ground, Santa makes an appearance at the fish pier, candy canes are being made, carriage rides are being taken, and of course, people are strolling around in their winter warmest clothes, enjoying every single second of this festival.
Naturally Beautiful
The natural side of Chatham offers its own charms and is guaranteed to make every picture you take appear as if a professional has taken it. It is nearly impossible to take a bad picture outside in Chatham and these outdoor Chatham, Cape Cod things to do will give you a peek into the serene, tranquil, and a little bit of the wild side of our Cape Cod hometown.
Monomoy National Wildlife Refuge, 30 Wikis Way
There are eight different refuges that make up the Eastern Massachusetts National Wildlife Refuge Complex, and the Monomoy National Wildlife Refuge is one of those important eight. Protecting the wildlife that inhabit its nearly 8000 acres, including migratory birds, gray seals, and horseshoe crabs and as you explore its paths and walkways, you will learn just how much each of the creatures are important to the life we lead, even if we can’t see them on a regular basis.
Beachcomber Boat Tours, 174 Crowell Road
Some of the most beautiful parts of Chatham are on the water and Beachcomber Boat Tours let’s travelers explore that part of our world. Offering seal tours along the Chatham Waterways, the Beachcomber is known for its banana color and shape, taking tourists to the places where the seal’s play and the scenery takes their breath away. Private charters are offered and many of the happiest people we have ever met have been married aboard one of the company’s larger boats, witnessed by friends, family, and of course, Beachcomber staff.
Kate Gould Park, 15 Chatham Bars Avenue
A walk in the park, in Kate Gould Park to be more precise, is destined to be a favorite activity, even if you aren’t visiting while the pumpkin people are residing there. Offering a classic gazebo which is where Friday concerts are held in the summer months and all generations of family members dance and sing along to the tunes being played, this park isn’t one you go to have a picnic or to play on a playground, but it is the centerpiece to almost every event that takes place in Chatham, giving visitors a better chance of learning the town a little better.
Follow the Scent of Our Best Restaurants
The best vacations often revolve around the meals we devour and our Chatham restaurants are sure to give you stories to tell, all good ones of course, and the restaurants listed below are a great start to your taste tour of Cape Cod.
Chatham Filling Station, 75 Old Harbor Road
The Chatham Filling Station is not a gas station, it is one of our favorite brunch spots, their brunches are so good they serve it all day! Closed on Wednesdays and Thursdays, the menu is filled with all your favorite breakfast foods, including their Station Breakfast Sandwich and an extensive Benedict section. This wonderful restaurant offers the best way to start your day and can also be a great lunch spot as well.
Wild Goose Tavern, 512 Main Street, Open Daily at 11:30
Speaking of lunch, colorful murals on the walls of the Wild Goose Tavern remind us that life isn’t meant to be serious all the time, especially the one with the geese bellying up to the bar. Offering a little of this, a little of that, and a lot of seafood dishes, the convivial vibe, delicious foods, and creative cocktails will make this eatery one of your favorites and you may even find yourself going back for dinner.
The Chatham Squire, 487 Main Street, Open 11:30 to 1 AM Daily
Whether you are coming to the Chatham Squire for lunch, dinner, or drinks and entertainment, the Chatham Squire will not let you down. Also offering a Sunday brunch, the Squire has been a local tradition since 1958 and if you come all this way and don’t visit the Chatham Squire, can you really feel you have explored all Chatham has to offer? This local hot spot is one we highly recommend at Pretty Picky Properties.
Come Home to Chatham and Our Pretty Picky Properties Retreats
No matter how you fill the minutes of your dream vacation in Chatham, coming home to our Pretty Picky Properties vacation retreats will provide the perfect ending to each beautiful day. Offering all the comforts of home, guests can choose rentals that provide as many as eight bedrooms, giving each traveler their own space to retreat to when the moon is high in the sky and as few as two bedrooms, for those more intimate escapes to the Cape. We pay attention to all the details that make vacation life comfortable and easy and there will be lobster pots in the kitchens, and because we understand the importance of having fun, there may even be game rooms, theater rooms, swimming pools, and hot tubs for your entertainment purposes!
Every Chatham Adventure Begins and Ends with Pretty Picky Properties
Reserve your favorite Chatham retreat today and be prepared to be the envy of all your friends, family, and acquaintances that weren’t able to accompany you on this trip of a lifetime!
Your Cape Cod vacation in Orleans is going to be one filled with beautiful beaches, scenic views, delicious seafood, and because you chose Pretty Picky Properties for your vacation accommodations, one that is more comfortable than any you have experienced before. If you’re looking for a place that offers relaxation, visit Orleans and discover why it’s one of Cape Cod’s best-kept secrets. The town of Orleans isn’t as well-known as some of the other towns and villages on the Cape, so today we want to give our guests a tour of everything that makes this town special, homing in on some of the top sights and attractions and leading the way back home to our Orleans retreat at day’s end.
This ultimate guide to Orleans may not make your decision of where to stay any easier, but it will give you a deeper understanding of Cape Cod and all the wonderful things you have to look forward to when you finally land on our sandy shores.
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Welcome to the South Parish of Eastham!
We can see the question mark in your eyes from here as you curl your brow and think to yourself, “I thought we were exploring Orleans?” So, no, we haven’t pulled the rug out from under you, we are just referring to Orleans original name, given to it many centuries ago. Settled in 1644 and incorporated in 1797, at which time the South Parish of Eastham was given the name of Orleans, throughout the years, the sea—more precisely, the fishing industry—was the chief source of employment and income for those that lived here, and until the Cape Cod Canal was built, this area experienced a plethora of shipwrecks.
Today, Orleans is remembered for being the only US site to have been attacked by Germans during WWII, when a German U-boat fired upon the tug Perth Amboy and four barges in the Nauset area, but that wasn’t its first brush with wartime issues. During the war of 1812, Rock Harbor was the site of a British attack, as the Brits fought to get America back under rule of the crown, obviously failing in the overall attempt, as well as failing to overtake Orleans, thanks to the dedicated response from our local militia.
It’s Always a Good Day at the Beach
Orleans is a beautiful town, and we know you will fall in love with it, probably within seconds of arriving, but we also know what drew you to our sandy shores and that would be those sandy shores themselves. A day at the beach on Cape Cod has been an all-American dream almost since travel was made simpler with the Cape Cod Railway, and your dreams are about to come true with a visit to Nauset Beach.
Offering 10 miles of coastline, the warmer waters make it an ideal spot for swimmers, surfers, and body boarders, and on some sections of the beach, Over Sand Vehicles (OSV) are allowed with the proper permit. Lifeguards are on duty from June through September, making moms from all over the world feel safer about their kids’ swimming adventures, and starting on the first Monday in July, the Nauset Beach Concert Series adds free music to your beachy adventures, with local musicians performing rock, blues, jazz, and so many other music genres at the Nauset Beach Gazebo. This is a popular beach, so plan on arriving early in order to get a prime spot and if you bring a cooler filled with food and beverages you don’t have to leave until after the sun sets; Nauset Beach is also a prime sunset watching location!
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Top Attractions and Things to Do in Orleans
As we mentioned earlier, Orleans isn’t as well-known as some of Cape Cods other towns, but we can assure you that there are some pretty cool attractions located within city limits, with our favorites listed below.
Jonathan Young Windmill, 41 Old Kings Highway
There are a few windmills you can see during your Massachusetts journey, but the Jonathan Young Windmill is unique in the fact that it still has all its original parts and machinery, something those other windmills can’t claim. Built in the early 18th century, it was moved from its original location in South Orleans to the Overlook on Town Cove in 1839 before moving to its current location after some relatively recent renovations. Sitting at water’s edge in a small park that offers stunning views, great fishing, and picnic tables, the windmill was once used to grind grain for settlers meals. Today, it serves as a reminder of those simpler times, providing a great selfie spot, and as you pose in front of the windmill, we’re sure you will get all the likes on your favorite social media sites!
French Cable Station Museum 41 S Orleans Road, Open Weekends 1PM-4PM
Back in the days before internet, people kept in touch through telegraph stations and the French Cable Station provided a direct connection to France, even going as far as to be known as “Le Direct.” Installed in 1891, the cable used for this purpose was over 3000 miles long, if you can imagine, and the station stayed in use until 1952, except for a few years during WWII when it was shut down for security purposes. Remember, Orleans was the site of the only attack by Germans during that war, and so it wouldn’t have been a stretch to imagine that the cable could have been used with ulterior motives during wartime. Today, it serves as a reminder of those simpler times, offering a variety of artifacts that are displayed throughout the museum, with some of the equipment found inside actually still being operational.
Addison Art Gallery, 43 S Orleans Road
Some of the world’s most talented artists make their homes in Orleans, and the Addison Art Gallery displays the best of their creations, including wood sculptures, paintings, and photography with most of the subject matter being life on Cape Cod. This display of art never fails to amaze us and presents the most unique of Orleans souvenirs; just one painting of a silent canoe sitting at shore’s edge at sunset will forever remind you of the sunsets you fell in love with during your stay!
Celebrating Orleans
Have you ever visited someplace new and come across an art show, a carnival, even a founders day celebration? Being able to attend this surprise events makes you love the place you are visiting even more, feeling a part of their town and making you want to return again to see what other wonderful surprises are in store for you. When you visit Orleans during the dates listed below, you will get to experience that wonderful sense of belonging for yourself and the memories you will make will be even sweeter!
Cherry Blossom Festival/Market in the Park, Mother’s Day Weekend, Orleans Village Green
Spring has sprung by the time Mother’s Day Weekend rolls around, and after our long and snowy winter, we are more than ready to celebrate cherry blossoms, sunshine, and the really cool things being sold by local vendors! Offering live music and the opportunity to dance around the figurative May Pole (ok, there’s no May Pole, but there WILL be dancing), those traveling with children will be delighted to learn that there is a kids’ craft area with outdoor activities for them to enjoy as well and perhaps be even more delighted to explore the food trucks and refreshments supplied by Truro Vineyards and Hog Island Beer Company. (We know we sure were.) This event is a free one, but don’t leave your wallet behind; you’ve got a lot of shopping to do, and that wine, beer, and food isn’t free!
Nauset Summer Crafts Festival, August, Nauset Regional Middle School, 70 MA-28
We envy the talents of local arts and artisans, wishing we shared in their skills, but since we don’t, we eagerly await the Nauset Summer Crafts Festival held every August at our Nauset Regional Middle School. This two-day event is known for offering 75 juried all-American handmade arts and crafts, as well as specialty food sampling booths where guests can enjoy a taste of homemade jams, sauces, candy, seasoning, even gourmet nut butters, with each sample convincing us that, yes, we need that product at home. Free demonstrations may encourage you to try your hand at crafting or jelly making, and free entry and parking ensure that you will have more money to spend on cool gifts and delicious treats!
Outermost Roots & Blues Festival, October, Nauset Beach
By October, most of Cape Cod has returned to its normal quiet and peaceful self, and although tourist season is over, Orleans find this month is the perfect month to celebrate music at the beach. The Outermost Roots & Blues Festival, held every October since 2018 (with the exception of a couple of COVID years), serves as a reminder that music and beach days should always go hand in hand, and as the music plays, the sea roars, and guests find themselves dancing in the sand, you too will be a fan of this exciting festival in Orleans, perhaps returning every year just to dance.
A Taste of Orleans
Now it is time to partake in everyone’s favorite part of vacation life, savoring a taste of Orleans at these amazing Cape Cod restaurants listed below. We’ve done the research, repeatedly on occasion, and we can assure you that these wonderful spots will be where your best meal memories are made!
Homeport Restaurant, 55 Main Street, Open Daily at 6AM
There’s an old bit of advice that tells us we should eat breakfast like a rich person would, lunch like a middle class person would, and dinner like we don’t have two cents to our names. Of course, this was meant as a way of making sure we don’t overeat, but it still leads us Homeport Restaurant for breakfasts that are hearty and delicious. A neighborhood staple for over 50 years, Homeport is also a favored lunch and dinner spot as they are open until 9PM every day except Tuesday, when they close at 2. Serving meals created with locally sourced ingredients, don’t ask us what our favorite meal is because every dish that we try is our favorite at the moment. We will say that the pancakes are fluffy, the omelets are laden with ingredients, and their benedicts are sensational!
Mahoney’s Atlantic Bar & Grill, 28 Main Street, Closed Sundays
You’re on Cape Cod, and when it is time to eat, you want to eat like you are on Cape Cod, and Mahoney’s Atlantic Bar & Grill is our first suggestion while in Orleans. Offering a New England menu that includes an authentic clam chowder and a pan roasted lobster that will make your taste buds cry with joy, whatever you order, be sure to save room for Baby Cake Gingerbread or our personal favorite, Molten Chocolate Cake! Their Chocolate Dessert Martini is pretty special as well, so sip away if you just can’t eat another bite.
The Beacon Room, 23 West Road, Closed Mondays & Tuesdays
Is your vacation to Cape Cod a celebration of an anniversary, a birthday, or some other special occasion? Or are you just in the mood to celebrate a Friday in paradise with a fantastic meal? Either way, the Beacon Room will provide a meal worth celebrating, serving a classic Italian seafood menu with class and skill. Offering a romantic patio under a tent so that the elements won’t intrude on your delicious meal, this fantastic restaurant is also known for its holiday meals that help take the burden off mom! We guess the downside to eating here is when you try their Faroe Island Salmon and you will never be satisfied with ordinary salmon again, but sometimes you just have to take the good with the bad.
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Find Happiness at Home with Pretty Picky Properties
All our Lower Cape vacation rentals are uniquely beautiful and wonderfully comfortable and the ones we offer in Orleans are sure to fit your family’s needs, like a fine leather glove. Offering properties with as few as 2 bedrooms or as many as 6, they also come equipped with an extensive list of amenities that can include swimming pools, hot tubs, water views, firepits, and so much more. Reserve your favorite Pretty Picky Properties Orleans retreat today and come home to comfort every night of your stay!
The towns and villages that make up the landscape of Cape Cod all offer their own distinctive personalities and when you get to know the ones you choose to stay in, we at Pretty Picky Properties believe it will increase your enjoyment of your vacation. Today, we want to introduce you to the town of Harwich, located in the heart of Barnstable County, comprised of seven villages, and offering a small-town charm that will truly make you fall in love. This ultimate guide to things to do in Harwich and all its villages will make you realize that vacation dreams can come true, especially when you choose Cape Cod for your destination and our Harwich retreats for your vacation accommodations!
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A Step Back in Time
We feel that to truly understand where a town is today you must visit its past, learning about all that made it strong and vital, and with Harwich, we really need to step way back in time. Originally settled in 1670, it was incorporated in 1694, originally including Brewster in its boundaries, a place that is now its own town and in which you can also find a selection of Pretty Picky Properties Cape Cod escapes.
The seven villages of Harwich are Harwich Center, East Harwich, Harwich Port, North Harwich, Pleasant Lake, South Harwich, and West Harwich, and just like the towns that make up Cape Cod, the vibe and personality of each village is varied. Harwich Port was known for its trade, while South Harwich and Pleasant Lake thrived due to the railroad, and North Harwich became known for its cranberry bogs, known as the birthplace of the cranberry industry with some bogs still in use today, offering tours for any who are interested. South and East Harwich, however, were far more isolated and even as they are thriving villages today, they retain much of their early charm, with very little being changed over the centuries of its existence.
Find Your Happy in Harwich
Originally named after an English seaport that Queen Elizabeth nicknamed Happy-Go-Lucky Harwich, you might think it would be impossible to be anything but happy when living, or visiting, this beautiful town, and you would be right. Once acclaimed as the “2nd happiest seaside town” (Thank you, Coastal Living magazine!), today, visitors and residents alike glow with joy as they go about their daily lives.
Providing nearly 11 miles of shoreline and five harbors, visitors can’t help but want to spend as much time as possible at the beach, with Red River Beach being one of the most popular, especially for families. Offering warm waters that are clear and calm, its soft sands might be where the best sandcastle you have ever built will be constructed, but even if sandcastle architecture is above your skill level, this is a beautiful beach for frolicking in the surf, kayaking and canoeing, and looking for shells, sea glass, or other beachcomber treasures!
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Top Harwich Activities and Attractions
There is always something exciting and fun going on in Harwich. Whether you are a history buff anxious to explore old buildings, are curious about the cranberry bogs you have seen in those Ocean Spray commercials, or are just going with the flow, meandering through the town and its villages stopping when you see something that interests you, the attractions listed below should definitely be added to your itinerary.
Cranberry Bog Tours, 1601 Factory Road in Harwich, Open Daily from 9 AM to 5 PM
We are the birthplace of the cranberry industry, and it is quite fascinating to see the process, so of course the first site you want to visit would be an authentic cranberry bog with Cranberry Bog Tours. Tour season begins in April, so if you are a winter visitor you may want to consider a return trip during the warmer seasons. Also, the public tours (costing $20 per person) are adults only, but if you are traveling with kids, you don’t have to skip this activity; you can purchase a private tour which you may enjoy more anyway. Be sure to leave time in your schedule to explore the farm stand, offering everything cranberry for sale, including honeys, soaps, and a cookbook that will be a delicious and colorful addition to your cookbook shelves at home.
South Harwich Meeting House, 270 Chatham Road in Harwich
Built in 1836, the South Harwich Meeting House is a simple structure that has stood the test of time. The meeting house was once the social and religious center of Harwich. Built in the Greek and Gothic design style, its two entrances were originally designed to separate the sexes, men used one, women used the other. Surrounded by the tombstones of former Harwich residents now engaged in resting peacefully, the meeting house is tranquil, serene, and currently used as a cultural arts center offering chamber music concerts, live theater performances, and so much more.
Cape Cod Lavender Farm, Off Weston Woods Road in Harwich, Open Daily 10AM-4PM
There must be something in the soil of Harwich that makes it especially fertile, seeing as two of our major attractions are both plant related. The Cape Cod Lavender Farm is one of our favorite places to visit, offering the divine aroma and many health benefits of this most colorful flower. This is a newer business, only having opened the gates to its blooms in 1995, but it has still become one of the most popular attractions on Cape Cod, offering an Enchanted Garden that both adults and children adore. Meandering through the fairytale that is the Enchanted Garden will capture the imagination of your children as they explore a magical castle built from stones and many faerie house portals throughout its expanse.
An onsite shop sells everything lavender related, including soaps, calming teas, sachets, candles, even lavender hibiscus lemonade, lavender spices, and herbs. Even better, their online store allows you to continue purchasing your favorite merch, even as you live thousands of miles away from the farm.
Celebrating Harwich
Attending the special events that take place throughout the year can add an extra sparkle to your already glowing getaway, so if you are in town during any of the below dates, we encourage you to drop by and see what else makes Harwich shine bright!
Cape Cod Baseball League, Opening Day in June, BFC Whitehouse Field
The Cape Cod Baseball League is a summer league offering roots that go back to 1885, even as it wasn’t officially formed until 1923. For over 100 years, our nation’s best players have played for teams such as the Brewster White Caps, the Chatham Anglers, and our personal favorite, the Harwich Mariners. (Whitehouse Field is the Mariners home stadium) Regarded as a premier collegiate summer baseball league, tomorrow’s superstars make an appearance every summer, allowing sports fans to truthfully say “I saw them when!” With over 370 active alumni playing in the major leagues currently, and over 1600 all-time, you might think that the CCBL is mighty important to a player’s success, and we think you are right! If you are visiting over 4th of July, there are usually games playing, ones that end with a spectacular fireworks display that will truly make you glad to be an American.
Harwich Cranberry Arts & Music Festival, September, Harwich Community Center
For two days in mid-September, the not so humble cranberry takes a starring role in one of the premier festivals on Cape Cod, the Harwich Cranberry Arts & Music Festival. Offering a minimum of 150 juried crafters, vendor tables, a kids’ area with crafts and games, food trucks, dining spaces, wine and beer sales, and of course, two afternoons of nonstop music, guests must bring their own chairs and/or blankets, but a dance floor IS provided for your enjoyment! It doesn’t cost anything to attend or to park, but you will need your money to shop, dine, and drink.
Time to Dine
Vacation meals are truly going to be worthy of dreaming about when you explore these fantastic Harwich area restaurants, and we apologize in advance over how much you will love each and every one. You are going to be obsessed and you will start considering a move to the Cape, just so that you can enjoy each meal whenever you want!
Cape Sea Grille, 31 Sea Street in Harwich Port, Open Wednesday-Sunday for Dinner
Combining history with deliciousness, the Cape Sea Grille is located inside a 19th century ship captain’s home featuring high ceilings, windows that stretch from floor to ceiling, and a genteel vibe that makes it the perfect special occasion restaurant. The menu of this charming restaurant is considered New American, and if you are looking for some ordering ideas, we suggest starting with their East Dennis Oysters for starters, their lobster, shrimp, and scallops for the main entrée, (seafood is locally sourced) and we heartily recommend saving room for their warm pecan tart, served with vanilla ice cream and caramel sauce. Their wine, beer, and cocktail menu is sheer perfection, so you may want to consider a designated driver!
Ruggie’s Breakfast & Lunch, 707 Main Street in Harwich, Open Daily at 6AM
Our mothers taught us that breakfast is the most important meal of the day, and even though your Pretty Picky Properties Harwich retreat does offer a fully equipped kitchen, we do hope you manage to make it to Ruggie’s at least once during your stay. The charming red painted house on Main Street has been the place to enjoy a hearty breakfast for about 15 years now, offering made from scratch dishes that taste like they did come from our mom’s kitchens. The Ruggie, a fried egg with cheddar cheese, sausage, and Ruggie’s cheese sauce served on a grilled bulky roll holds a special place in our heart, especially when we throw caution to the wind and upgrade to their cheese & gravy home fries!
Brax Landing, 705 MA-28 in Harwich Port, Open Daily, 11:30AM to 10PM
You must enjoy waterfront dining at least once during your Harwich adventures, and Brax Landing is surprisingly inexpensive for a waterfront eatery. Offering a menu filled with runners and swimmers (surf and turf), this is THE spot to get an authentic lobster roll, and their “chowdah” is pretty special as well. Harbor views make every bite taste even more delicious and summer visitors cannot sip enough of their frozen cocktails, with the Godzilla, a strawberry pina colada, being our absolute fave!
Have We Covered It All?
The town of Harwich and its seven villages are exciting places to visit, and as you explore all the things to do in Harwich, in the back of your mind, the thought of your Pretty Picky Properties Harwich retreat may be lingering. The comfort, luxury, and style that each offer, plus the water views that many offer as well, just beg to be explored, and if you can tear yourself away from cranberry bogs and baseball games for one day at home, we think you will be even more pleased with your vacation experiences. Our Harwich escapes are plentiful, ranging in size from cozy 2-bedroom cottages to spacious 7-bedroom retreats. All offer a large selection of amenities—swimming pools in some, firepits in many, and all the comforts in every space we offer. Your time spent at home will be the most relaxing moments of your escape to the Cape!
The Experience Matters
A vacation home is just as important to the success of your getaway as the sites you see and the foods you eat, and we do have not forgotten that very important fact. Maybe you will do nothing more than sit in front of a roaring fire on a chilly summer night, sipping wine, and sharing quiet conversations with your favorite traveling partner or maybe your entire family will gather round the dining table on a rainy night, fighting over who gets to the be the dog in Monopoly and laughing late into the night. The experience of feeling welcomed, cherished, and at home in your Pretty Picky Properties Harwich sanctuary will be one you will never forget. Reserve your favorite escape today!
What’s better than a summer vacation on Cape Cod? A summer vacation that’s perfectly planned so you can spend more time relaxing and less time stressing. With its charming coastal towns, beautiful beaches, and endless activities, Cape Cod is the ultimate summer destination for families, couples, and groups of friends looking to soak up the sun and enjoy classic New England charm. The key to a stress-free getaway is planning early, ensuring you get the best accommodations, dining experiences, and activities lined up before the summer crowds arrive.
Explore the Best of Cape Cod’s Outdoor Activities
Summer on Cape Cod is all about enjoying the great outdoors. The region is home to some of the most stunning beaches in New England, each offering a unique experience. Whether you prefer the gentle waves of Mayflower Beach, the scenic beauty of Nauset Beach, or the iconic dunes of Race Point Beach, there’s a perfect stretch of sand for everyone. Early planning means you can secure parking permits, reserve beach chairs and umbrellas, and even plan a beachfront picnic without any last-minute hassle.
Beyond the beaches, Cape Cod offers an abundance of outdoor activities. Bike along the Cape Cod Rail Trail, a scenic path that winds through picturesque towns and woodlands. Take a kayak or paddleboard out on one of the many inlets and bays, where you can explore tranquil waters and spot local wildlife. Whale-watching tours are another must-do, with excursions departing from Provincetown and Barnstable giving you a chance to see majestic whales in their natural habitat. If you love fishing, chartering a boat for a deep-sea fishing trip is an experience that shouldn’t be missed.
Savor the Flavors of Cape Cod
Food is an essential part of any summer vacation, and Cape Cod delivers with some of the freshest seafood and classic coastal cuisine. Lobster rolls, fried clams, and clam chowder are staples that every visitor must try. Planning ahead and making reservations at some of the most popular waterfront restaurants ensures you won’t miss out on these delicious experiences. From casual seafood shacks to fine dining overlooking the ocean, Cape Cod’s dining scene offers something for every taste and occasion.
For those who love a good brew or a craft cocktail, Cape Cod’s breweries and wineries provide the perfect spots to relax and unwind. Spend an afternoon tasting local wines or sampling craft beers at one of the area’s laid-back taprooms. Many spots feature outdoor seating, live music, and beautiful views, creating a perfect setting for a leisurely summer afternoon.
Experience the Cape’s Unique Attractions and Events
Beyond its beaches and seafood, Cape Cod is rich with cultural and historical attractions. Take a ferry to Martha’s Vineyard or Nantucket for a day of island exploration, where you can visit charming boutiques, tour historic lighthouses, and enjoy scenic bike rides. The Cape is also home to fascinating museums, including the Cape Cod Maritime Museum and Heritage Museums & Gardens, which provide insight into the region’s seafaring past and natural beauty.
Summer on Cape Cod is also filled with exciting events, from art festivals and live music performances to farmers’ markets and outdoor movie nights. Planning your trip early allows you to check event calendars and incorporate these unique experiences into your itinerary. Whether you’re interested in an old-fashioned clambake, a scenic sunset cruise, or a lively Fourth of July celebration, Cape Cod has something special for every visitor.
Book Your Summer Getaway with Pretty Picky Properties
Finding the perfect place to stay is just as important as planning your activities. Pretty Picky Properties offers a wide selection of vacation rentals across Cape Cod, ensuring you have a home base that suits your needs. Whether you’re looking for a waterfront escape, a pet-friendly retreat, or a luxury property with all the amenities, there’s a perfect rental waiting for you. With properties available in Brewster, Dennis, Yarmouth, and beyond, you can stay close to your favorite attractions while enjoying the comforts of home.
Booking early means you get the first pick of the best rentals, ensuring you secure a property that fits your group size and vacation style. Many of these rentals come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces perfect for relaxing after a day of exploring. Whether you want to wake up to ocean views or enjoy a private backyard with a fire pit, planning ahead allows you to find the ideal summer getaway spot.
Start Planning Your Cape Cod Summer Escape Today
A Cape Cod summer vacation is one of the best ways to enjoy sun, sand, and classic New England charm. With a little early planning, you can secure the best accommodations, line up exciting activities, and make restaurant reservations before the summer crowds arrive. Book your dream vacation rental with Pretty Picky Properties today!
Are you wondering where you should celebrate Easter this year? With its charming coastal towns, fresh ocean air, and festive springtime events, Cape Cod is a perfect destination for an Easter getaway. Whether you’re looking for a peaceful retreat by the water, a delicious holiday brunch, or fun-filled activities for the kids, Cape Cod for Easter has something special to offer.
Easter Egg Hunts and Family Festivities
Easter on Cape Cod is all about family-friendly fun. Towns across the Cape host a variety of Easter egg hunts, making it a perfect destination for kids and families looking for a festive spring break. Places like Chatham, Hyannis, and Dennis put on fantastic egg hunts in local parks and community centers, offering kids the thrill of collecting colorful eggs and prizes. Many of these events also feature visits from the Easter Bunny, live music, face painting, and other entertainment that makes for a fun-filled day.
For a unique twist on the traditional Easter egg hunt, check out the Sandwich Glass Museum’s annual Easter celebration. The museum often hosts glass-blowing demonstrations and special Easter-themed art exhibits, making it a great option for those who appreciate history and craftsmanship.
Easter Brunch on Cape Cod
No Easter celebration is complete without a delicious brunch, and Cape Cod’s restaurants and inns serve up some of the best holiday meals in New England. Many of the Cape’s top dining spots offer special Easter menus featuring fresh seafood, carved meats, and decadent desserts.
The Chatham Bars Inn is known for hosting an elegant Easter brunch with stunning ocean views. Their holiday menu features farm-to-table ingredients, seasonal specialties, and an assortment of mouthwatering desserts. In Hyannis, The Red Jacket Beach Resort also offers a fantastic Easter buffet with classic breakfast favorites and coastal-inspired dishes.
For a more casual setting, many local cafés and bakeries offer delightful Easter morning pastries, including hot cross buns, fruit tarts, and homemade muffins. If you prefer to have a relaxed Easter meal at home, you can even pick up a pre-made feast from one of the Cape’s gourmet markets and enjoy a holiday meal in the comfort of your vacation rental.
Explore the Natural Beauty of Cape Cod
Spring is a wonderful time to experience the natural beauty of Cape Cod. The warmer temperatures and blooming landscapes make it perfect for outdoor adventures. Take a scenic walk along the Cape Cod National Seashore and enjoy breathtaking views of the Atlantic Ocean. The trails at Nickerson State Park in Brewster provide a picturesque setting for a peaceful Easter morning hike.
For those who love biking, the Cape Cod Rail Trail is a fantastic way to explore the region’s charming villages and coastal scenery. The 25-mile trail runs through towns like Orleans, Brewster, and Dennis, offering plenty of opportunities to stop for coffee, take in the views, and soak in the fresh spring air.
If you’re a fan of wildlife, consider visiting the Wellfleet Bay Wildlife Sanctuary, where you can observe birds and other native species in their natural habitats. Spring is a great time to see migratory birds returning to the area, adding another special touch to your Easter getaway.
Book Your Cape Cod Easter Rental with Pretty Picky Properties
A Cape Cod getaway wouldn’t be complete without a comfortable and charming place to stay. Instead of booking a small hotel room, why not enjoy the space and privacy of a vacation rental with Pretty Picky Properties?
At Pretty Picky Properties, we offer a range of beautiful vacation rentals suited for groups of all sizes. Whether you’re visiting with a small group of friends or the entire family, we have the perfect home for you. Our rentals feature fantastic amenities, including pet-friendly options, private pools, waterfront properties, and luxury homes that provide an unforgettable Cape Cod experience.
Our vacation rentals are conveniently located throughout the Cape, including Dennis, Yarmouth, Brewster, and beyond, making it easy for you to explore everything the region has to offer. Whether you’re looking for a cozy home near the beach or a spacious house for a large gathering, Pretty Picky Properties has the ideal rental for your Easter vacation.
Make the Most of Your Cape Cod Easter Getaway
Start planning your Easter 2025 getaway today and book your ideal vacation rental with Pretty Picky Properties. With stunning accommodations and a prime location near Cape Cod’s best attractions, your Easter escape will be filled with relaxation, adventure, and lasting memories.
Springtime on Cape Cod is a breath of fresh air – literally. The crowds of summer haven’t arrived yet, the flowers are in bloom, and the crisp ocean breeze makes every outdoor activity feel like an adventure. Whether you’re looking to explore nature, enjoy the waterfront, or simply relax in the fresh air, Cape Cod offers plenty of options for a perfect spring getaway. Here are some of the best outdoor activities on Cape Cod to enjoy during this refreshing season.
Hit the Cape Cod National Seashore
Spring is the perfect time to visit the Cape Cod National Seashore before the summer rush begins. Stretching over 40 miles, this stunning stretch of protected coastline offers hiking trails, picturesque dunes, and some of the most beautiful beaches in New England. Marconi Beach and Race Point Beach are both fantastic spots to take in the scenery, enjoy a quiet picnic, or go for a brisk seaside walk. With fewer people around, you’ll get to experience the natural beauty of the Cape at your own pace.
Explore the Cape Cod Rail Trail
Cycling enthusiasts will love the Cape Cod Rail Trail, a 25-mile path that takes you through some of the most scenic areas of the Cape. Running from South Dennis to Wellfleet, this paved trail winds through charming towns, salt marshes, and pine forests, offering plenty of opportunities to stop and explore. Bring your own bike or rent one from a local shop along the way. Spring’s cooler temperatures make it one of the best times of the year to ride.
Take a Whale Watching Tour
Spring marks the return of whales to the waters off Cape Cod, making it an ideal time for a whale-watching tour. Humpback, minke, and finback whales migrate back to the area in the spring, and the waters near Provincetown are one of the best places in the world to see them. Book a tour with a local operator and prepare for an awe-inspiring experience as these majestic creatures breach and play in the Atlantic.
Visit the Cape’s Historic Lighthouses
Cape Cod is home to some of the most iconic lighthouses in New England, and spring is a great time to explore them without the summer crowds. Nauset Light in Eastham, Highland Light in Truro, and Chatham Light in Chatham all offer incredible views and a glimpse into the maritime history of the region. Many lighthouses offer guided tours, so you can learn about their history and significance while enjoying the fresh ocean air.
Go Kayaking or Paddleboarding
The waterways of Cape Cod come alive in the spring, making it the perfect season for kayaking or paddleboarding. Places like Pleasant Bay, Nauset Marsh, and the Bass River provide calm, scenic paddling routes where you can spot wildlife and enjoy the peaceful surroundings. If you don’t have your own gear, rental shops and guided tours are available throughout the Cape to help you get out on the water with ease.
Enjoy a Springtime Stroll Through Cape Cod’s Gardens
Cape Cod’s gardens start blooming in the spring, creating a colorful display of flowers and plants. The Heritage Museums & Gardens in Sandwich is a must-visit spot, featuring 100 acres of lush gardens, walking trails, and beautiful exhibits. The rhododendron and daffodil blooms in spring are truly spectacular. Even just a casual stroll through Cape Cod’s small towns will reveal charming gardens and window boxes filled with fresh spring flowers.
Book Your Spring Rental with Pretty Picky Properties
Spring is a perfect time to unwind and reset, and there’s no better place to do that than in a vacation rental tailored to your needs. We at Pretty Picky Properties offer a range of vacation homes across Cape Cod, including Brewster, Chatham, Orleans, Yarmouth, Dennis, and beyond. Whether you’re looking for a waterfront retreat, a home with beach access, a pet-friendly rental, or a property with a pool, we have something to fit your vacation style. Whether you’re visiting with a small group of friends or bringing the entire family, our properties provide the comfort and amenities you need for a relaxing and memorable stay.
Plan Your Cape Cod Spring Escape Today
Spring is the perfect season to experience the beauty of Cape Cod without the summer crowds. Whether you’re biking the Rail Trail, exploring historic lighthouses, or kayaking through peaceful waters, there’s something for everyone to enjoy. Make the most of your Cape Cod adventure by booking a stay with Pretty Picky Properties, where comfort, convenience, and stunning locations come together to create the ultimate getaway. Browse our selection of vacation rentals today and start planning your spring escape to Cape Cod!
Spring Break is a time to relax, recharge, and make some great memories, and there’s no better place to do that than beautiful Cape Cod. While many associate Cape Cod with summer, the early spring months offer a peaceful, scenic, and enjoyable way to experience this coastal gem. Whether you’re looking to enjoy outdoor adventures, local cuisine, or just unwind by the water, Cape Cod for spring break has plenty to offer.
Embrace the Outdoors
One of the best things about Cape Cod is its natural beauty, and during Spring Break, you can fully embrace the great outdoors. Spring on Cape Cod is quieter than the busy summer months, giving you a chance to enjoy the area’s many scenic hiking trails without the crowds.
Take a stroll through Cape Cod National Seashore. This 43,000-acre park offers over 40 miles of pristine beaches, salt marshes, and scenic walking trails. You can walk along the beach, hike through the dunes, or just sit and watch the waves crash against the shore. For those looking for a more challenging hike, the Great Island Trail in Wellfleet is a beautiful, more rugged option, offering views of Cape Cod Bay and the surrounding wilderness.
Even in the spring, Cape Cod’s beaches are a sight to behold. While the water might still be too chilly for swimming, the beaches are perfect for long walks, picnics, or just soaking in the breathtaking views. Nauset Beach in Orleans is known for its expansive shoreline and is a great spot for beachcombing or simply relaxing with a good book.
Explore the Towns and Villages
Cape Cod is made up of charming towns and villages, each with its own unique character. During Spring Break, it’s the perfect time to wander around these quaint communities without the summer crowds.
Start in Hyannis, the commercial heart of Cape Cod. Here you’ll find a variety of restaurants, shops, and cafes to explore. Stop by the Cape Cod Mall or the Main Street area, where you can shop for local artisan goods, Cape Cod-themed souvenirs, and unique treasures. While the weather might not be beach-friendly in early spring, it’s still a great time to enjoy the quaint ambiance of the town.
For a more laid-back vibe, head to Chatham. Known for its charming streets and the iconic Chatham Lighthouse, this town offers a perfect combination of shopping, art galleries, and dining. Explore the quaint Main Street, visit Chatham’s Fish Pier, and grab a bite at one of the cozy restaurants offering fresh seafood.
If you’re looking for something a little more off the beaten path, Brewster is a quieter village that’s perfect for those who want to get away from the crowds. Known for its peaceful beaches and natural beauty, Brewster is the ideal spot to enjoy a relaxing day.
Take a Scenic Boat Tour
While it might be too cold for a swim, a boat tour around Cape Cod is an excellent way to see the beauty of the area from a different perspective. Many local operators offer scenic tours of Cape Cod Bay, where you can enjoy views of the shoreline, wildlife, and historic lighthouses.
In the spring, whale watching is also an option, with several boat tours offering excursions to see migrating whales. Keep an eye out for seals, dolphins, and various seabirds, too!
If you’re looking for something more tranquil, The Cape Cod Canal offers boat rentals where you can enjoy a peaceful ride along the water, taking in the beauty of the surrounding area. Visiting for the Cape Cod Canal Day? Choose our vacation rentals on Cape Cod, Massachusetts and celebrate this day in style!
Relax and Recharge at Your Vacation Rental
After a day of outdoor adventures or exploring the towns of Cape Cod, there’s no better way to unwind than by retreating to a cozy, comfortable vacation rental. And with Pretty Picky Properties, you’re sure to find the perfect spot to make your Cape Cod Spring Break even more special.
We offer a wide selection of beautiful vacation rentals on Cape Cod, including luxury homes, pet-friendly properties, waterfront homes, and rentals with hot tubs. Whether you’re planning a romantic getaway, a family vacation, or a solo retreat, we have something to suit every need.
If you’re traveling with family or friends, their spacious homes provide ample room to relax and enjoy quality time together. Many of our homes offer large living areas, fully equipped kitchens, and private outdoor spaces where you can enjoy a barbecue or a relaxing evening under the stars. You’ll also enjoy the convenience of being near popular attractions, with many of the properties located in Dennis, Hyannis, Brewster, Yarmouth, and beyond.
Book with Pretty Picky Properties
When you book a vacation rental with Pretty Picky Properties, you’re setting yourself up for an unforgettable Cape Cod experience. With spacious, fully equipped homes and a range of amenities to suit your needs, you’ll have everything you need for a relaxing and enjoyable stay. Book your stay today and start planning the Spring Break of your dreams on Cape Cod!
Valentine’s Day is the perfect occasion to show your loved one just how much they mean to you. If you’re looking for a romantic getaway that combines natural beauty, charm, and plenty of opportunities for indulgence, Cape Cod should be at the top of your list. Here’s how you can spoil your loved one on Cape Cod for Valentine’s Day!
Start the Day with a Cozy Breakfast
Kick off Valentine’s Day with a cozy breakfast. Cape Cod offers plenty of charming spots for a warm and delicious meal, or you can enjoy a homemade breakfast in your rental. If you’re staying in a vacation home, consider preparing something special with fresh local produce, eggs, or seafood. Lobster omelets, fruit salads, or pancakes with maple syrup are all easy ways to add a personal touch and start the day off right.
Stroll Along Scenic Beaches
Cape Cod’s beaches are breathtaking year-round, and Valentine’s Day is no exception. Even in the colder months, a quiet walk along the shore with your partner can feel incredibly romantic. Bundle up in cozy sweaters, hold hands, and enjoy the sound of the waves crashing against the shore as you take in the stunning views of the ocean.
For a truly intimate experience, head to one of Cape Cod’s more secluded beaches, where you can enjoy each other’s company without the distractions of crowds. Whether you’re walking along the beach or simply sitting on the sand, this is the perfect place to connect.
Take a Scenic Drive Through the Cape
Cape Cod’s winding roads and coastal landscapes make for the perfect backdrop for a scenic drive. Grab a map or use your phone to find some of the most picturesque spots on the Cape. Take a relaxing drive through charming towns like Brewster, Yarmouth, or Chatham, where you can enjoy beautiful views of the ocean, quaint cottages, and historical landmarks. Stop along the way for some photo opportunities, whether it’s at one of Cape Cod’s iconic lighthouses or in front of a vibrant town square.
Go Wine Tasting or Visit Local Shops
Cape Cod boasts a variety of wineries and local shops perfect for a leisurely afternoon out. Spend some time browsing through artisan shops, galleries, and boutiques where you can pick up a unique piece of Cape Cod to take home. There’s nothing more thoughtful than a handmade gift that captures the essence of your getaway.
For a special treat, consider booking a wine tasting experience at one of the local wineries. Many offer cozy settings with beautiful vineyard views, perfect for sharing a glass of wine with your loved one. Whether you prefer a dry red or a crisp white, you’ll enjoy tasting the local flavors while spending quality time together.
Unwind with a Spa Day
Valentine’s Day is all about relaxation, and what better way to unwind than with a rejuvenating spa day? Cape Cod offers several spas and wellness centers that specialize in couples’ treatments, including massages, facials, and more. Book a couple’s massage where you can both relax side by side, letting go of any stress and embracing the peaceful atmosphere.
Many of the spas also offer specialty Valentine’s Day packages, such as champagne and chocolate treatments, which add a little extra indulgence to your day.
Find Your Cape Cod Valentine’s Day Rental with Pretty Picky Properties
The key to a truly unforgettable Valentine’s Day getaway is where you stay. Instead of booking a typical hotel room, why not rent a private home or cottage where you and your loved one can enjoy some privacy and comfort? Pretty Picky Properties offers a large selection of vacation rentals across Cape Cod, including Yarmouth, Brewster, and beyond.
With Pretty Picky Properties, you can find the perfect home that suits your romantic escape, whether it’s a cozy cottage or a luxurious beachfront property. Our homes come with a range of amenities designed to make your stay as relaxing and enjoyable as possible. You can choose from properties that are pet-friendly, or even luxury options with stunning views. Each property is carefully curated to ensure a high standard of comfort and charm, making it the ideal place to enjoy your romantic Valentine’s Day getaway.
Start Planning Your Romantic Getaway
Cape Cod is the ultimate destination to spoil your loved one this Valentine’s Day. From scenic beach walks and cozy breakfasts to spa treatments and sunset cruises, there’s no shortage of romantic activities to enjoy. Contact us to book your romantic escape today and make this Valentine’s Day one to remember.
If you’re planning a trip to the stunning beaches of Cape Cod, 2025 is the perfect year to take advantage of Book Direct Day, happening on February 5th! Whether you’re visiting to explore the charming towns, enjoy the incredible seafood, or just relax by the water, you can make the most of your vacation by booking directly with property owners and managers. Discover why booking direct is the way to go for your Cape Cod getaway!
The Benefits of Booking Direct on Book Direct Day
Booking directly with a vacation rental property has its perks, and Book Direct Day is a great reminder of all the advantages it offers. One of the biggest draws of booking direct is the cost savings. When you book through third-party websites like Airbnb or Vrbo, you’re often hit with hidden fees and service charges that can add a significant amount to your total bill, usually 10%-15%. These fees, though convenient for the platform, don’t benefit you as the guest or the property owner.
By booking directly through a property management team or individual owner, you can avoid those pesky third-party commissions and fees. That means more of your money goes to your vacation instead of to the platform. In fact, many property managers offer exclusive discounts, special packages, or lower rates for guests who book directly. So not only can you save money by booking direct, but you can also often get a better deal than you would on a third-party site.
Better Communication Means a Better Stay
Booking directly gives you the opportunity to communicate personally with the property manager, which leads to a more customized and personalized experience. Have a special request? Need an early check-in or late check-out? Want to add something extra to your stay, like arranging a surprise welcome basket or special accommodations for your pet? When you book through a third-party platform, all communication is filtered through the platform, which can sometimes slow down the process or limit the flexibility of what’s possible.
When you book directly, you have direct access to our team, meaning any special requests, questions, or concerns can be addressed quickly and efficiently. Whether it’s finding the perfect property for your family, customizing your experience with local recommendations, or ensuring you have everything you need for a stress-free stay, booking direct allows you to get the most out of your trip.
A Stay Tailored Just for You
One of the biggest advantages of booking directly with property managers is the flexibility and customization that it offers. Booking platforms like Airbnb or Vrbo often follow a rigid set of guidelines when it comes to your stay, such as check-in times, room selection, cancellation policies, and so on. While these policies might work for some, they don’t always provide the freedom to cater to your personal needs.
When you book directly, the experience becomes much more flexible and customizable. You’ll have the opportunity to speak directly with the property manager to request changes or special accommodations, such as a late check-out, a different room layout, or even specific amenities that suit your trip’s purpose.
Perks for Returning Guests
If you plan to make Cape Cod a regular vacation destination, you’ll want to take advantage of the loyalty rewards that many property managers offer to repeat guests. By booking directly, you can often receive exclusive perks for your return visit, including discounts, free upgrades, or even additional amenities that are available only to loyal customers. These rewards are a great way to feel valued and appreciated as a guest, and they can make your future visits to Cape Cod even more special.
Support Local Businesses and the Cape Cod Economy
When you choose to book directly with a local business like Pretty Picky Properties, you’re supporting small businesses and contributing to the local economy. Large third-party platforms often take a substantial cut of the booking fee, meaning much of your payment goes to the platform, not to the local property owners who are working hard to maintain their vacation rentals. By booking directly, more of your money stays in the local community, helping to support the Cape Cod economy and the people who make it such a wonderful place to visit.
Book Your Stay with Pretty Picky Properties
If you’re looking for a Cape Cod vacation experience that’s more personal, more affordable, and more memorable, look no further than Pretty Picky Properties. We offer a wide range of beautiful vacation rentals across Cape Cod, including Brewster, Yarmouth, Dennis, Chatham, Eastham and beyond.
Looking to head up north? Check out our Wellfleet vacation rentals! Whether you’re visiting for a solo retreat, a romantic couples getaway, or a family vacation, we have a property that will put a smile on your face.
Our vacation rentals are designed with comfort and style in mind, offering everything you need for the perfect getaway. From luxurious amenities like private pools and hot tubs to pet-friendly properties and last-minute availability, we’ve got you covered. And since we specialize in properties with water views and close proximity to Cape Cod’s best beaches, you can enjoy all that the area has to offer without venturing too far from your rental.
Plan Your Perfect Cape Cod Getaway
As you plan your 2025 Cape Cod adventure, remember that booking directly has so many benefits that can enhance your stay. From the cost savings and flexibility to personalized communication and the satisfaction of supporting local businesses, booking with Pretty Picky Properties is the smart choice for your Cape Cod vacation. Book your stay today and get ready to enjoy the perfect Cape Cod getaway!
The new year is a time for fresh starts and bold resolutions, so why not make yours the promise of adventure and relaxation? Cape Cod, Massachusetts is a dream destination that offers the perfect combination of natural beauty, charming towns, and exciting activities to help you start 2025 on a high note. Whether you’re looking for a romantic getaway, a family vacation, or a solo retreat, Cape Cod for New Year’s is a destination for anyone.
A Bucket-List Destination
Cape Cod is a destination that feels like stepping into a postcard. With its iconic lighthouses, stunning beaches, and quaint villages, it has a timeless appeal that draws visitors year after year. But beyond its picturesque charm, Cape Cod offers a wide range of activities and experiences for travelers of all ages and interests.
Outdoor enthusiasts can explore Cape Cod’s miles of sandy beaches, scenic biking trails, and lush nature preserves. Food lovers will delight in the area’s fresh seafood and farm-to-table dining options. History buffs can explore the Cape’s rich maritime heritage through its many museums and historical sites. No matter what kind of traveler you are, Cape Cod offers something special to discover.
When Is the Best Time to Visit Cape Cod?
While Cape Cod is a popular summer destination, each season brings its own unique charm. If your 2025 resolution includes fewer crowds and a slower pace, consider visiting in the spring or fall. In spring, the Cape comes alive with blooming flowers and migratory birds, offering mild temperatures and ideal conditions for outdoor adventures.
Fall is equally magical, with crisp air, golden foliage, and quieter beaches. It’s also a great time for foodies, as the Cape’s local seafood shines during harvest season. Summer, of course, remains the peak season for a reason. It’s when the Cape is buzzing with festivals, outdoor concerts, and lively beach days. No matter when you choose to visit, Cape Cod promises a memorable experience.
What Cape Cod Offers Travelers
Cape Cod is the perfect destination for relaxation and exploration. Begin your mornings with a walk along the beach, watching the sunrise over the Atlantic Ocean. Spend your afternoons biking along the Cape Cod Rail Trail, a scenic 25-mile route that winds through quaint villages and wooded areas. The trail is family-friendly, making it a wonderful activity for groups of all ages.
For those who love the water, Cape Cod offers fantastic fishing, kayaking, paddleboarding, and even whale-watching tours during the warmer months. Visiting in the fall or winter? Bundle up and explore the Cape’s many hiking trails, like those at the Wellfleet Bay Wildlife Sanctuary, where stunning views and peaceful settings abound.
Cape Cod’s vibrant towns also offer unique shopping experiences. From antique shops in Sandwich to art galleries in Provincetown, you’ll find treasures to bring home as a reminder of your trip. End your days with fresh seafood at one of the Cape’s celebrated dining spots. Lobster rolls, clam chowder, and oysters are local specialties you won’t want to miss.
Your Home Away from Home with Pretty Picky Properties
One of the best ways to experience Cape Cod is by staying in a vacation rental that feels like your own private retreat. With Pretty Picky Properties, you’ll find a stunning selection of homes across Cape Cod’s most desirable communities, including Chatham, Orleans, Wellfleet, and Yarmouth.
Our rentals are designed to suit a variety of travel styles and group sizes. Looking for a luxury waterfront home? We’ve got you covered. Traveling with a pet? Check out our pet-friendly rentals that welcome every member of the family. Dreaming of a house with a private pool? You’ll find it in our portfolio.
Each property is thoughtfully furnished and equipped with amenities like fully equipped kitchens, spacious living areas, and outdoor spaces perfect for relaxing or entertaining. Staying in a vacation rental also allows you to cook your own meals, offering a convenient way to save money while enjoying quality time with loved ones.
With Pretty Picky Properties, you’ll have a home base that makes exploring Cape Cod seamless and enjoyable.
Plan Your Cape Cod New Year’s Escape Today
Cape Cod is calling, and there’s no better time to answer than 2025. Whether you’re looking to relax by the ocean, explore charming villages, or savor the freshest seafood around, this timeless destination has something for everyone.
Book your Cape Cod vacation rental with Pretty Picky Properties today and start planning your perfect getaway. With stunning homes, exceptional service, and all the beauty of Cape Cod waiting for you, your New Year’s resolution is about to become your favorite adventure yet.