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 to enjoy on Cape Cod 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 has plenty to offer during Spring Break.
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.
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 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.
A Cape Cod vacation is destined to be one of the greatest vacation you have ever taken, no matter which community, town, or village you choose to stay in, but there are ones that we at Pretty Picky Properties believe will truly enhance your vacation experience. The sun appears to shine brighter, the beaches seem warmer and more welcoming, and because we refuse to offer anything less than the best for our guests, you will find our Cape Cod vacation retreats luxuriously residing within the city limits. This guide to the top Cape Cod communities will give you a better idea of what to expect and help you to narrow down your final destination to the community that best fits your family’s needs.
Barnstable, Founded in 1639
Barnstable is one of the oldest communities on Cape Cod, steeped in history and offering seven charming villages, many of which we will be discussing further down the page. Home to the Olde Colonial Courthouse built in 1774, making it one of the oldest Colonial buildings in the country, the rich history, stunning views, and natural landscape will ensure that there is always something wonderful to do or see without having to travel far. The best time to visit is (and this will pretty much stay the same for all communities unless otherwise noted) in the months of May, June, September, and October, as the weather will be wonderful, and the crowds will be smaller. We like to call it “Locals Summer”. Below, we have listed some of our favorite Barnstable activities, attractions, and restaurants.
Sandy Neck Beach Park
Offering a 6.5-mile-long barrier beach with dunes that can reach up to 100 feet tall, Sandy Neck Beach Park is popular with hikers, bird watchers, swimmers, and drivers, as the beach can be driven on with offroad vehicles with the proper permit.
Barnstable Comedy Club, 3171 Main Street
Barnstable’s long history means it features a lot of “the oldest” businesses, buildings, etc., and the Barnstable Comedy Club falls under the category of the oldest club in the area. Continually open for over 100 years, talented performers have helped guests lose themselves in the magic on the stage, and that magic continues today.
The Dolphin Restaurant, 3250 Main Street
There’s a reason long running restaurants last, and that reason is a complicated blend of staff, ambience, and of course, good food. The Dolphin Restaurant, in business for over 70 years, is the perfect example. Moderately priced and offering a menu filled with both surf and turf options, we have visited many times over the years and never had a bad experience. Seafood on Cape Cod is fresher and sweeter than what you may be used to, so if you are choosing between a burger and their shrimp and scallops, go for the latter. You can thank us later!
Brewster, Founded in 1803
Brewster is one of the newer Cape Cod areas founded in 1803. It was originally settled in the mid-1600s. Brewster is home to the largest pond on Cape Cod, coincidentally named Long Pond, and is nicknamed the Sea Captain’s Town due to the large number of sea captains who once settled there.
Brewster General Store, 1935 Main Street
Shopping is a popular activity during any vacation, and there is a large selection of stores in the area that we highly recommend, but perhaps the most fascinating one is the Brewster General Store. The building in which the store is housed was originally a church, but in 1866 it was converted into a general store and has been a primary source of candy, gifts, toys, and yummy ice cream ever since.
Stony Brook Grist Mill, 830 Stony Brook Road
Originally built in 1699, the grist mill was washed away in a storm. It was rebuilt on the same site in 1751 using beams from the original building. During the Revolutionary War, grains from the mill were taken to feed British soldiers, and today it is the last remaining building of Factory Village, a once thriving industrial part of Brewster. Open for tours on weekends during the spring and summer months, cornmeal is still made and sold at the mill, providing a unique souvenir for your travels.
Spinnaker Restaurant, 2019 Main Street
Reservations are required for Spinnaker Restaurant, one of our favorite Brewster special occasion eateries. The menu changes on a regular basis, and with each new rendition we grow to love it more, recommending that guests save room for dessert—in particular the chocolate dessert of the day!
Chatham, Incorporated in 1712
Although it wasn’t incorporated until 1712, Chatham was originally settled in 1685. Its charm and beauty stand out in the Cape Cod communities in that is renowned for both, so be sure to keep your camera handy when visiting.
Chatham Lighthouse, 37 Main Street
Constructed in 1808, the Chatham Lighthouse still shines its light over stormy waters today and during the season (July through September). Operating 24 hours a day, it stands 48 feet tall, and fortunately for tired travelers, it takes only 44 steps to reach the top.
Ducks in the Window, 507 Main Street
One of the quirkier stores on Cape Cod, Ducks in the Window is loved by all, as its shelves are filled with rubber ducks of all sizes and professions. Yes, we said professions, as there are police ducks, nurse ducks, even teacher ducks, and you can’t help but smile and be happy when you walk into the store for the first time.
The Chatham Squire, 487 Main Street
The Chatham Squire is a typical New England restaurant, featuring casual décor, a great bar, and good food that sticks to your ribs as you go about your touristy business. The bar side offers video games and foosball, while the dining side is a little more formal, providing a menu filled with seafood delights you will greatly miss when it is time to leave Cape Cod. Meet me at the Squire!
Dennis, Settled in 1639, Incorporated in 1793
The history of Dennis makes it a popular vacation destination for history buffs, offering a large variety of historic neighborhoods that visitors simply love to stroll about in.
The Cape Playhouse, 820 Main Street
Professional summer theater isn’t as big of a deal on the mainland as it once was, but on Cape Cod, it is integral to the Cape Cod experience, and the Cape Playhouse has been continuously running since 1927. Famous for Humphrey Bogart performing on its stage, you will feel a sense of history as you sit in the audience, perhaps imagining what it would have been like to watch the talented Humphrey Bogart performing.
All American Town of Dennis Fireworks
The end of summer is always a sad time for Cape Cod, but the party that sends off our guests with a bang is something to look forward to. Featuring a Hallmark movie style bonfire on the West Dennis Beach, there will be live music, the opportunity to roast marshmallows, and the big burst of colorful explosions in the sky, all guaranteed to make this farewell to summer shine a little brighter.
Grumpy’s, 1408 Main Street in East Dennis
Breakfast is the most important meal of the day, and when you enjoy it at Grumpy’s, we can promise you won’t leave grumpy or unsatisfied. Grumpy’s selection of benedicts boggles the mind, and if you are here long enough, you may want to work your way through each dish.
Harwich, Founded in 1665 and Incorporated in 1694
Cranberry bogs have been a huge part of Cape Cod for over 200 years, with Harwich being the town most commonly associated with the colorful fruit. Harwich has been named as America’s second happiest seaside town.
The Harwich Cranberry Arts & Music Festival, Weekends in September
One of our favorite local festivals, the Harwich Cranberry Arts & Music Festival pays homage to the cranberry with food trucks, live music, and a wooden dance floor in a tent, as well as over 150 craft vendors selling jewelry, art, gifts, and handmade foods. The best way to get to know the area you are visiting is by attending its local festivals, and this end of season festival will bring you joy.
Watch the Harwich Mariners Win a Game
The Cape Cod Baseball League is where tomorrow’s superstars perfect their game, with some of the MLB’s biggest players having hit a homerun with their traditional wooden bats. Thurman Munson, Jason Varitek, Aaron Judge, and many, many more have played on these hallowed fields, and who knows? Maybe the players you are watching today will be tomorrow’s superstars.
Cape Sea Grille, 31 Sea Street in Harwich Port
Housed inside a former sea captain’s home, Cape Sea Grille is a wonderful special occasion spot serving new American cuisine. Open year round and offering elevated selections of surf or turf meals, their braised pork Osso Busco is a dish dreams are made of.
Hyannis Port, Founded in 1639
Hyannis Port has a long history, but perhaps its most famed time were the years the Kennedys made the village their playground. The Kennedy compound has been the summer home for the Kennedys since the 1920s, when Joseph Kennedy first rented the initial cottage for a summer vacation. The family still owns the compound, and the widow of Robert F. Kennedy actually lived there until her death in October of 2024.
John F. Kennedy Hyannis Museum, 397 Main Street in Hyannis
The Kennedy name was much loved in this part of Cape Cod, on all of Cape Cod, and the JFK Hyannis Museum pays proper homage to the hero whose life was cut too short. Hyannis Port was always considered the heart and home of the Kennedys, and the museum doesn’t stop at chronicling JFK’s life but touches on all the Kennedys who lived and loved here through the years.
Baxter’s Wharf Restaurant & Waterfront Dining, 177 Pleasant Street in Hyannis
We can’t help but focus on the Kennedys when discussing Hyannis Port, and we aren’t going to stop with the restaurant suggestion. Baxter’s Wharf Restaurant was known to be where the Kennedys ate often, and if you had visited during that time, chances are you may have dined in the same room as the President, his brother, or any of the numerous family members who made Cape Cod their home in the summer months.
Orleans, Settled in 1693
Orleans is the only US site attacked during WWII, when a German U-boat fired at the tug, Perth Amboy. Today, it is known for its beautiful landscape, arts scene, and its history that began long before the U-boat incident, an incident that Disney made a movie about in 2016.
Jonathan Young Windmill, 41 Old Kings Highway in Orleans
Most people do not know that there are seven windmills on Cape Cod, with the Jonathan Young Windmill being built in the early 18th century. It is a unique part of our history, still offering original parts that actually work. Open to the public in July and August, the windmill took a circuitous route to get to where it stands today, having been built in South Orleans, moved to the center of town, then to Hyannisport, then returned to its current location.
The Alley Bowling & BBQ, 191 MA-6 in Orleans
Combining the fun of candlepin bowling and the yum of house smoked barbecue, the Alley Bowling & BBQ may be your favorite Cape Cod experience of all. Candlepin bowling is played with smaller balls and thinner pins and is a sport that originated right here in New England. Barbecue may not be a food that is unique to Cape Cod, but we assure you that you will find no beef with their beef!
We Are There
The best communities of Cape Cod have one major thing in common: our Pretty Picky Properties are located in each and every one! Offering comfort, style, and a quiet New England luxury, our properties will become an integral part of your vacation experience. Reserve your favorite today!
Once upon a time, Sundays were set aside to spend time with extended family. Sunday dinners at grandma’s house were common activities. We played with cousins who would always be considered our first friends, ate homemade meals that the diet police would not approve of, and savored the familiarity of family. Times have changed, and those special moments don’t happen very often, making family reunions a vital way of keeping the family close, and when you really want to make the family reunion special, choosing to take it on the road to Cape Cod is a great idea. Choosing Pretty Picky Properties for your vacation accommodations is an even better one, as these 10 reasons to plan your family reunion on Cape Cod will show!
Reason #10: You Have Always Wanted to Visit Cape Cod
Sometimes the simplest reasons are the most compelling ones, and wanting to visit Cape Cod can be the best reason of all to plan your family reunion there. You’ve been dreaming about it for years, saving your pennies so you can afford to do it right, and now it is time for your vacation dreams to come true. Cape Cod has been a much-loved vacation destination for over 100 years, and we can guarantee that you aren’t the only one in your family that has dreamed about visiting, ensuring that other vacation dreams will come true as well. Welcoming families with charm, history, and a variety of ways to play together or separately, your family reunion on Cape Cod will be one that is never forgotten.
Reason #9: A Beach Vacation Is an American Tradition
A family vacation at the beach is a long-standing tradition that is also one of life’s greatest luxuries, and when you get to share that same vacation with your extended family, it elevates the experience exponentially. As mentioned earlier, your cousins were your first friends, but are your children’s cousins theirs? Chances are they only get together for funerals and family reunions, making your family vacation to Cape Cod vital in helping them forge deeper bonds. Many of our Pretty Picky Properties are located on or near the Cape Cod National Seashore, and the cousins can work on building their bonds as they work together to build sandcastles at shore’s edge. Renting a boat and towing the squealing youngsters on rafts or innertubes will be another bond tightening experience and because our homes offer entertainment options as well as comfort and luxury, they can also work to put together large puzzles throughout their stay. And as you hang out with your own parents, grandparents, and cousins, reminiscing about the crazy times you and your cousins shared during your growing up years will help you rebuild yours.
Reason #8: Educational and Entertaining
As parents, we want our children to do well in a world that doesn’t always make it easy to do so, and part of helping to ensure that they do can be accomplished by education. On the plus side, every experience can be a lesson learned, but on the negative side, our children often fail to see the fun or importance. And so, just like we hide pills in treats for our dogs, we hide education in entertainment, taking them to science museums where interactive activities are fun and attention grabbing. On Cape Cod, history surrounds you and even as the adults in your group appreciate walking in the footsteps of our ancestors, your children may just think its “cool” exploring some of the more historical spots, spots that will unbeknownst to them offer a history lesson they will enjoy.
Hoxie House, 18 Water Street in Sandwich
Reputed to be one of the oldest houses on Cape Cod, Hoxie House was built circa 1640, over 100 years before our nation fought for its independence, and the tours offered of this ancient home will give guests a fascinating peek into that time period. Holding what may be the oldest surviving loom in America and serving as a meeting place for Reverend John Smith, the artifacts from colonial times will surprise your kids due to their simplicity.
Whydah Pirates Museum, 674 MA-28 in West Yarmouth
There is absolutely no doubt in our minds that everyone in your family will be fascinated by the Whydah Pirates Museum. The artifacts displayed in this museum were recovered from an 18th century ship used for piracy, and the replica of a pirate ship that can be found here will capture the imagination of your youngest family members. Inexpensive, (admittance fees run between $14 and $16) the history lessons learned from the museum will never be recognized as lessons at all.
Reason #7: The Perfect Backdrop for Family Photos
Just as the weekly family dinner has gone by the wayside, so have family pictures, and if you are like us, the last family picture taken may be missing the newest additions to the family. A family reunion on Cape Cod, however, offers the perfect backdrops for taking updated pics that the matriarch will cry over when she sees them. We’ve listed some of our favorite spots for taking family photos below.
Mayflower Beach in Dennis
Countless family photos have been taken at the beaches of Cape Cod over the past two centuries, and any beach on the Cape will work as a backdrop, but Mayflower Beach offers miles of flats and wavy patterns in the sand that will add interest to your picture. Don matching attire (white shirts and blue jeans are the most common clothing worn in family beach pictures) and head to the beach at sunset, taking pictures filled with color and serenity, and of course, all of your favorite people.
Chatham Lighthouse in Chatham
The lighthouses of Cape Cod have served as backdrops for pictures for as long as we can remember, and although the Nauset Lighthouse, the one pictured on the bag of Cape Cod Potato Chips, may be the most well-known lighthouse, the Chatham Lighthouse is one that we feel offers the most charm. Standing tall and proud as it does its duty of protecting the ships in the area from harm, the lighthouse keeper’s home and its red roof add an extra element of wow to any photos taken here!
Reason #6: Activities for Large Groups
The problem with traveling with large groups lies solely in the realization that there may not be many activities the group can participate in together. Beach days, of course, are always an option on Cape Cod, but there are many other activities that large groups can partake in during a family vacation to Cape Cod, some of which are listed below.
Cape Cod Harbor Tour, 715 Main Street in Harwich Port
A sunset cruise is a traditional Cape Cod adventure, one that you may not think you can participate in when you are traveling with a large group, but Cape Cod Harbor Tour’s newest boat, the White Shark, offers room for up to 45 guests, and their sunset cocktail cruise promises to be an adventure your entire family will enjoy. The kids can sip soft drinks as they eat their ice cream, but the cash bar offering cocktails, local wines, beer, and snacks ensures that you will be comfortably happy as you and your large group watch the sun fall into the sea.
Hiking
The natural landscape of Cape Cod will make you want to spend as much time as possible outside playing, something that is easy for larger groups to do. There are many different hiking trails that traverse the cape, offering a wonderful way to learn the beauty of the area. Gray’s Beach Boardwalk in Yarmouth Port offers a quick family friendly hike that is accessible for hikers of all ages and skill levels, extending out over the marsh and offering views of the landscape, the sea, and all its inhabitants that will change the feel of your family reunion getaway.
Reason #5: The Cape Cod Rail Trail
Another popular group activity is a ride along the Cape Cod Rail Trail, extending out 26 miles and passing through six different Cape Cod towns, most of which you will find Pretty Picky Properties located in. Following alongside the old railroad tracks that used to bring tourists and supplies to various towns throughout Cape Cod, riders can rent bikes from a variety of shops, most of which are located on or near the trail. Passing through the towns of Yarmouth, Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet, the changing land and seascape never fails to fascinate. The Rail Trail Bike & Kayak Rentals, 302 Underpass Road in Brewster, offers a large selection of bike and bike gear rentals as well as providing direct access to the trail.
Reason #4: Restaurants that can Handle Large Groups
Our Pretty Picky Properties retreats feature large and fully equipped kitchens that will make meal prep fun and easy, but you don’t want to be stuck at home creating every meal, especially as the restaurants of Cape Cod offer delicious meals that are prepared, served, and cleared away by someone other than you!
Freeman’s Grill, 1000 Freeman’s Way in Brewster
Located on the Captain’s Golf Course and offering all the space you need for a large group seeking sustenance and suds, Freeman’s Grill in Brewster is destined to be your favorite dining spot when hitting the town.
The Skipper Restaurant & Chowder House, 152 S Shore Drive in South Yarmouth
Open seasonally, the Skipper Restaurant & Chowder House is a Cape Cod tradition, one that you can experience with your large group. One of the oldest restaurants on the Cape, the views of Nantucket Sound will make the perfect accompaniment to your seafood dinner and Skipper’s Ice Cream Shack will make the perfect ending to a beautiful meal with family.
Reason #3: The Family That Fishes Together Eats Well
There is nothing like a fish dinner caught and grilled yourself, and when the family joins in the fun, the quiet hours between bites are destined to be filled with laughter and fish stories about the ones that got away. (They weren’t there, so how would they know?) And although you are perfectly capable of renting a boat and heading out blindly to spots where you can drop a line and cross your fingers, hoping for a bite or three, or you could hire a charter, one in which the captains know all the hopping spots, practically guaranteeing you will catch your limit. If the latter sounds best to you, Cape Cod Family Charters, 200 Millway in Barnstable is, of course, the only charter company we would recommend for your family fishing adventures. Offering 4-, 5-, or 6-hour expeditions, the captains will take your family out to catch a boat load (Is that where the term came from?) of striped bass, bluefish, tuna, and cod, and at trip’s end, will take the obligatory picture of your haul, which of course you can share on social media, earning the envy of all your friends back home.
Reason #2: Tour of Lighthouses
Did you know that there are 14 lighthouses on Cape Cod, including Chatham Lighthouse, where you took your family photo, and Nauset Lighthouse, which you have been seeing on the bag of your favorite Cape Cod Potato Chips for years. No trip to Cape Cod would be complete without a visit to at least one of the lighthouses, taking the tours and climbing all the stairs, but if you really want to show off, you can visit them all. Highland Lighthouse is a bit of a drive, being located in North Truro, but as it the oldest and tallest lighthouse on Cape Cod and was commissioned by George Washington himself in 1797, it definitely is worth the little extra effort!
Reason #1: Our Pretty Picky Properties Make Luxurious and Spacious Accommodations
Pretty Picky Properties is named as such due to the fact that we are pretty picky about the properties we offer, which means your family reunion vacation is that much more comfortable and luxurious. Our largest homes offer as many as 10 bedrooms and room for 20 to 24 people while also providing a large selection of luxury amenities that can include private swimming pools, hot tubs, and game rooms that will encourage your loving family to stay home and play on days when everyone is feeling especially comfy! Firepits and outdoor kitchens will entice you to engage in family barbecues and storytelling sessions that last long into the night, and large porches lined with rockers will be where everyone sits to watch the sun set every evening of their stay. Check out our 8-bedroom Cape Cod mansion rentals that include ample private space for everyone!
Looking for a refreshing and unique way to kick off the New Year? Trade the hustle and bustle of crowded city celebrations for the charm of Cape Cod. This quintessential New England destination might be famous for its summer vibes, but the Cape has plenty of magic to offer in winter, especially during New Year’s. From cozy celebrations to crisp seaside walks and local festivities, a Cape Cod New Year’s trip is the perfect mix of relaxation and adventure.
Cozy Up to New England Charm
Cape Cod in winter has a special kind of magic. The crowds are gone, and the charming towns are beautifully peaceful, with twinkling lights and that quintessential coastal coziness. Picture yourself strolling along historic Main Streets in towns like Chatham or Provincetown, bundled up with a warm drink in hand, as you pop into quaint shops and admire the festive window displays.
While you’re there, stop by local bakeries and cafes for treats like fresh-baked pastries or a cup of clam chowder to warm your soul. Many shops and restaurants remain open year-round, and you’ll love the slower pace and welcoming atmosphere that Cape Cod is famous for.
Cape Cod New Year’s Eve Festivities
If you’re looking for festive ways to celebrate New Year’s Eve on the Cape, there are plenty of fun options to explore!
One of the highlights is First Night Chatham, an annual celebration that transforms the town into a family-friendly New Year’s wonderland. With ice sculptures, live music, kids’ activities, and a magical early countdown for the little ones, it’s a great way to enjoy the holiday. The evening wraps up with a festive fireworks display over Oyster Pond, what better way to kick off the New Year?
If you’re in the mood for something a bit more relaxed, many local restaurants host special New Year’s Eve dinners. Book a cozy table at spots like The Red Inn in Provincetown or The Ocean House in Dennis, where you can enjoy fresh seafood, gourmet dishes, and celebratory cocktails.
Explore Cape Cod’s Natural Beauty
Cape Cod’s beauty isn’t limited to summer, its coastal charm is just as breathtaking in winter. Bundle up and explore the Cape’s natural wonders with fewer crowds and plenty of room to roam.
Take a brisk walk along the beach at Cape Cod National Seashore or visit the picturesque dunes in Wellfleet. The views are stunning, and the fresh sea air is the perfect way to reset after the holiday hustle. For a dose of wildlife, head to Monomoy National Wildlife Refuge in Chatham, where you might spot seals lounging along the shore.
Don’t forget to check out the Cape Cod Rail Trail for a peaceful winter hike or bike ride. This 25-mile path winds through charming towns, forests, and cranberry bogs, offering a unique perspective of the Cape’s winter beauty.
Celebrate at Your Cape Cod Vacation Rental
One of the best parts of spending Cape Cod New Year’s? You don’t need to go out to have an amazing time. In fact, some of the most memorable celebrations happen in the comfort of your vacation rental.
Many Cape Cod rentals offer cozy gas fireplaces, game rooms, and stunning views – perfect for a quiet evening or an intimate gathering. Plus, if you’re feeling festive, host your own countdown with a homemade dinner featuring local seafood (think lobster rolls or fresh oysters), pop some champagne, and enjoy the magic of New Year’s in a space that feels like home. Whether it’s relaxing in a spacious living room or watching the ball drop from your rental’s private deck, the possibilities are endless.
Stay with Pretty Picky Properties
Ready to plan your New Year’s trip to Cape Cod? At Pretty Picky Properties, we make it easy to find the perfect rental for your celebration. Whether you’re planning a quiet getaway or a lively family gathering, we have a variety of properties to suit every traveler and group size.
Many of our properties are pet-friendly, so you can even bring your furry friends along for the fun! From charming cottages to luxurious waterfront homes, there’s something for everyone.
Our rentals are conveniently located in some of Cape Cod’s most beloved towns, including Brewster, Chatham, Wellfleet, Yarmouth, and Dennis. No matter where you stay, you’ll be close to the area’s best attractions, restaurants, and natural beauty.
Make Your New Year’s Magical
Book your New Year’s adventure with Pretty Picky Properties today and get ready to experience the magic of Cape Cod this holiday season. Here’s to a New Year filled with joy, laughter, and unforgettable memories!
Cape Cod is the perfect place to capture holiday photos with family, offering a range of scenic spots from coastal views to charming historic towns. Whether you’re looking for sandy beaches, picturesque lighthouses, or cozy village settings, here’s a guide to some of the best spots for your holiday family photos on Cape Cod.
Chatham Lighthouse Beach
Chatham Lighthouse Beach is one of Cape Cod’s most iconic spots, with a view that captures both the beauty of the beach and the history of the area. The lighthouse itself, set against the Atlantic Ocean, provides a classic New England backdrop for family photos. During the holiday season, the nearby town of Chatham often decorates with seasonal touches, adding a bit of festive cheer to your beachside photos on Cape Cod.
The open stretch of beach makes it easy to find a spot with a beautiful view of the water or the lighthouse in the background. Early morning or late afternoon light works best here, giving your photos a warm, soft glow against the beach and lighthouse.
Brewster’s Old Mill
Brewster’s Old Mill is a lovely spot for family photos with its rustic charm and historic significance. Located in the heart of Brewster, the mill is surrounded by greenery, a small pond, and picturesque pathways. This setting feels straight out of a New England postcard, making it a perfect spot for family photos with a vintage feel.
During the holiday season, Brewster is often decorated with wreaths and lights, giving the area a cozy, festive vibe. Families can pose by the mill, along the pond’s edge, or on the small bridge nearby for a variety of holiday photo options.
Nobska Lighthouse
For families who want a stunning view with a bit of coastal drama, Nobska Lighthouse in Woods Hole is a fantastic choice. Perched on a hill overlooking Vineyard Sound, the lighthouse offers sweeping views of the water and is one of the most photographed lighthouses on Cape Cod. The white structure of the lighthouse contrasts beautifully with the deep blue ocean, creating a simple yet striking background for family photos.
Nobska Lighthouse is especially magical around sunset, when the light creates a warm glow over the water and the lighthouse. For family shots, gather near the base of the lighthouse or along the stone wall for a variety of different looks.
Heritage Museums & Gardens
If you’re looking for a spot with a bit of everything, Heritage Museums & Gardens in Sandwich is a wonderful choice. The gardens cover over 100 acres and include a variety of scenic settings, from manicured lawns to woodland trails. During the holiday season, Heritage Gardens often hosts a Gardens Aglow event, where thousands of lights illuminate the gardens, creating a festive and magical atmosphere. Families can pose by the light displays, under twinkling arches, or in front of the historic windmill that’s located on the property.
Main Street
For a cozy, small-town setting, Main Street in Hyannis offers the perfect mix of festive holiday decorations, historic charm, and local flavor. The street is lined with shops, restaurants, and seasonal decor, giving it a warm and welcoming feel that’s great for family photos. During the holidays, Main Street is often decorated with lights, wreaths, and garlands, making it a festive place to capture holiday memories.
Hyannis also has a beautiful Christmas tree displayed in the town square, which makes for a great backdrop for holiday photos on Cape Cod. The combination of local shops, holiday decor, and cheerful atmosphere creates a classic holiday setting.
Your Holiday Rental with Pretty Picky Properties
To make the most of your holiday experience on Cape Cod, book your stay with Pretty Picky Properties. We offer a range of beautiful vacation rentals across Cape Cod, including communities like Brewster, Yarmouth, Dennis, and beyond. Whether you’re planning a romantic getaway or a holiday retreat with the entire family, our selection of properties has something for everyone.
Enjoy your holiday getaway in one of our pet-friendly or luxury rentals, with amenities like fireplaces, ocean views, and spacious living areas perfect for relaxing with family. Staying with Pretty Picky Properties means you’ll be close to the best photo locations, allowing you to fully embrace the Cape Cod charm this holiday season.
Book Your Holiday Getaway to Cape Cod
Cape Cod’s mix of coastal views, charming villages, and festive decorations makes it an ideal destination for family holiday photos. Capture the spirit of the season with your loved ones in these beautiful settings, from iconic lighthouses to quaint town squares. Book your holiday stay with Pretty Picky Properties and make this holiday season one to remember on Cape Cod!
Are you ready to experience the charm of Cape Cod during the holidays? December on the Cape is full of festive events that blend coastal beauty with holiday cheer, making it a beautiful destination for seasonal fun. Whether you’re in the mood for holiday lights, unique markets, or Christmas parades, Cape Cod has something for everyone. Here’s a guide to the top holiday events on Cape Cod this season.
Lobster Pot Christmas Tree in Provincetown
One of Cape Cod’s most unique holiday displays, the Lobster Pot Christmas Tree is a beloved tradition in Provincetown. Located in Lopes Square, this “tree” is made entirely of stacked lobster pots, decorated with vibrant holiday lights, buoys, and other festive touches. It’s a whimsical tribute to Cape Cod’s fishing heritage and a must-see for visitors. Stop by in the evening to see the lights in full effect, perfect for photos or simply soaking up the holiday spirit. Families, couples, and solo travelers alike enjoy this quirky display, which adds a unique twist to holiday décor.
Gardens Aglow at Heritage Museums & Gardens
For a magical winter wonderland experience, Gardens Aglow at Heritage Museums & Gardens in Sandwich is a top destination. From mid-November through December, the gardens are transformed into a holiday spectacle, with over 10 miles of lights, decorated trees, and displays that illuminate the grounds. Visitors can stroll through the gardens while enjoying the cozy glow of lights, seasonal decorations, and music.
Families with young children especially love Gardens Aglow, as the event also includes activities like marshmallow roasting, holiday crafts, and opportunities for photos with Santa. There are even live performances, adding an extra festive touch to the evening. Tickets often sell out, so it’s wise to book in advance to experience this enchanting event.
Holidays By The Sea Weekend in Falmouth
One of the Cape’s biggest holiday events, Holidays By The Sea Weekend in Falmouth is a lively celebration held from December 6th to 8th. The weekend kicks off with a visit from Santa, who arrives by boat at Falmouth Harbor, followed by a festive tree lighting and caroling. The town’s Christmas Parade is a big draw, featuring colorful floats, marching bands, and a joyful crowd lining Main Street.
Holidays By The Sea is a true family event, with activities that engage visitors of all ages. Kids will love the chance to see Santa, while adults can enjoy the local vendors and festive treats available throughout the weekend. For a quintessential Cape Cod holiday experience, Falmouth’s celebration is a must.
Brewster for the Holidays
Another community-wide celebration, Brewster for the Holidays takes place over the first weekend in December, bringing together local businesses and residents for a weekend of festivities. The event features a holiday market, live music, tree lighting, and an array of activities across town. Visitors can explore local shops for holiday gifts, enjoy seasonal treats, and take part in family-friendly events on Cape Cod.
The holiday market is a favorite among locals and visitors, offering handmade crafts, artisanal goods, and Cape Cod-themed gifts. Families will find plenty to do, from kid-friendly activities to visits from Santa, creating a welcoming environment for everyone.
Book Your Holiday Stay with Pretty Picky Properties
After a day of exploring Cape Cod’s holiday events, relax in a cozy vacation rental with Pretty Picky Properties. We offer a wide range of beautiful homes throughout Cape Cod, catering to every type of traveler and group size. Whether you’re looking for a cozy escape with a fireplace, a rental with a private hot tub, or a spacious property for a family gathering, Pretty Picky Properties has the perfect option for you.
Our rentals are located in some of Cape Cod’s most popular communities, including Brewster, Chatham, Wellfleet, Dennis, and Hyannis. Each property is fully equipped with amenities like a full kitchen, comfortable living spaces, and beautiful views, so you can unwind in style after a day of holiday festivities. Choose from properties near the beach, close to town, or tucked away in a quiet neighborhood, providing the flexibility to plan your perfect Cape Cod getaway.
Plan Your Festive Cape Cod Escape
Cape Cod in December is filled with holiday charm and a lineup of events on Cape Cod that capture the magic of the season. From the unique Lobster Pot Christmas Tree to the dazzling lights at Gardens Aglow, the Cape offers something special for everyone. Make the most of your holiday visit by booking with Pretty Picky Properties! Contact us today!