Cape Cod Vacation Homes Archives - Pretty Picky Home Rentals
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Ready to kick off 2024 in style? Look no further than the charming shores of Cape Cod, Massachusetts. Nestled between the Atlantic Ocean and Cape Cod Bay, this coastal gem is gearing up to offer you a New Year’s celebration like no other. So, explore the many ways you can welcome the year ahead with a trip to Cape Cod.

Kick Off 2024 with a Trip to Cape Cod

Dive into the annual Polar Plunge at Bass River Beach in Yarmouth! Join the Friends of Yarmouth Council on Aging and make a splash with friends and family in the chilly Nantucket Sound on New Year’s Day at noon. It’s not just about conquering the cold – this is a community affair filled with camaraderie, laughter, and shared memories. After the daring dive, warm up with complimentary hot cocoa and baked goods. It’s a free, community give-back event that blends the thrill of the chill with the cozy comfort of community spirit. Embrace the unconventional and plunge into 2024 with a splash to remember!

Illuminate Your New Year

Get ready for a vibrant start to the New Year with Provincetown’s First Light Celebration, a multi-day event from December 29th to January 1st. The town comes alive with festivities, offering something for everyone. Wander through the two-day holiday market featuring local vendors, soak up the lively atmosphere with live entertainment. Don’t miss the community-loved Light Bright Bike Ride – a dazzling display of illuminated bicycles parading through the town. The highlight? Cap off the celebration with breathtaking fireworks at MacMillan Pier, casting a radiant glow over the waterfront.

Enjoy Comfort at Home

When it comes to kicking off the year in comfort and style, our vacation rentals on Cape Cod have you covered. Picture fully equipped properties designed to be your home away from home, offering everything you need for a memorable stay. Our kitchens are stocked and ready for your culinary adventures – cook up delicious dishes and savor them around the dining room table with friends and family.

As the temperatures drop, embrace the inviting charm of Cape Cod by spending your evenings in our cozy living rooms. Whether you’re planning a quiet night in or a festive gathering, our vacation rentals provide the perfect backdrop for a fantastic start to the year.

Explore Local Nightlife

As the sun sets on Cape Cod, its vibrant nightlife takes center stage, offering a variety of hotspots to suit every preference. From energetic venues with live music, DJs, and dance floors to laid-back spots featuring jazz shows and Italian cuisine, the options are as diverse as they are lively.

Head to emBargo in Barnstable for a taste of metropolitan chic – a stylish lounge with DJs, dancing, a raw bar, tapas, and even family-style pig roasts. If you’re in the mood for a more relaxed evening, swing by Roadhouse Café, where a nautical-themed lounge, a piano bar, live jazz, and delightful Italian dishes create the perfect ambiance. Whether you’re sipping on signature cocktails, enjoying craft beers at Barnstable Brewing, or hitting the dance floor, Cape Cod’s nightlife promises unforgettable moments.

Enjoy a Seaside Stroll

Step into the New Year with a sense of serenity by taking a leisurely walk along the pristine shores of Cape Cod. Whether you’re an early riser, relishing the quiet charm of the first light, or a sunset enthusiast bidding a fond farewell to the day, the calming waves and salty breeze create an ideal backdrop for reflection and anticipation. As you wander along the coastline, let the sound of the waves instill a sense of peace, setting the perfect tone for a year filled with new beginnings.

A Stylish Start to 2024

Give yourself the gift of a fresh start in the New Year by enjoying some retail therapy in Cape Cod. A new wardrobe is the perfect start to 2024, offering a stylish beginning to this chapter of your journey. Whether you’re into big-name brands, hidden boutiques, or thrifting adventures, Cape Cod’s shopping scene invites you to explore and curate a collection that reflects the upgraded, confident you. Step into the boutiques, discover local treasures, and create a wardrobe that sets the tone for a fabulous and fashionable year ahead.

Book Your Cape Cod Adventure Today

Wrapping up the many ways to kick off your New Year in Cape Cod, there’s no better way to seal the experience than by booking one of our properties. We offer rentals to suit every preference – from pet-friendly rentals and waterfront retreats to luxurious homes and properties featuring a refreshing pool. Whether you’re planning a cozy escape for two or a gathering with friends and family, our range of rentals ensures a perfect fit. Don’t miss the chance to turn your Cape Cod experience into an unforgettable stay. Contact us  Book your stay today!

A Cape Cod vacation is something that is on nearly everyone’s bucket list, and when your vacation destination dreams come true, it is only fair that the property you shelter in should be a vacation dream come true as well! We at Pretty Picky Properties understand what vacationers seek, and for the larger traveling groups Grayduck 207-C is a classic New England cottage rental with room for 10! Providing four spacious and serene bedrooms, three spa-like baths, and all the beauty for which a beach vacation is known, Grayduck is located just across the street from one of Chatham’s most stunning beaches. It’s also just a short distance from downtown, ensuring that every minute of your stay will be more than you dreamed it could be. This guide to its charms and wonders will give you a little something extra to look forward to in the days and weeks leading up to your escape to the Cape! 

Click here to Book today or read on for more info!

Better Than You Dreamed 

A brick pathway leads to the robin’s-egg blue front door tucked away under a large front porch dotted with white wood cushioned rockers, a spot where you may find yourself sitting on a warm summer’s eve, sipping a chilled Cape Codder and watching the goings-on in the neighborhood, enjoying the color of the hydrangea bushes flanking the entrance of the porch, and listening to the sounds of the sea located just across the street. Your Cape Cod vacation could be one filled with road trips, museum explorations, and sampling the restaurants of Chatham, or it could be one in which you slow down the pace, play at the beach, and explore all the comforts and amenities that Grayduck provides without leaving the property. 

Inside this beautiful escape property lies a world of peace, serenity, and farmhouse charm, a world backed up by shiplap walls painted a crisp white and in which the décor reflects the wonders of the sea. There’s a living room that is divided into two parts, one with a soft white sofa where quiet conversations are destined to be enjoyed. A second seating area surrounds a Smart TV where movie nights are bound to happen. The dining room of Grayduck is just off the kitchen, anchored by a large wood farmhouse table surrounded by enough seats for everyone in your party. Perched under lobster basket style lights, this room provides more than just a place to eat. It is the center of all that is wonderful about family. Playing board games late into the night, enjoying animated conversations over cups of coffee and bowls of cereal in the morning, and holding the pieces of a puzzle waiting to be put together, the memories you make in this room will last forever. 

The kitchen is another room where family gathers This one holds all the bells and whistles of a chef’s dream kitchen, including an impressive gas range, an expansive center island fronted with cushioned ratan barstools, and rows of windows that look out towards the Atlantic Ocean beyond. As in every properly equipped New England kitchen, a lobster pot is provided, and of course, the small appliances that make life better: a coffee pot, toaster, and blender for whipping up frothy tropical drinks! 

Offering two master bedrooms, Grayduck is the perfect vacation home for multiple families traveling together. Each master suite provides a king bed and an en suite full bath. Iron beds continue the theme of farmhouse chic, and high ceilings make large bedrooms appear even larger. One master suite offers a sitting area perfect for enjoying coffee in the mornings, and views of the beach give that bedroom a feeling of peace that will make you never want to leave. The bathrooms offer a beachy and whimsical style, one with lobster wallpaper and subway tiles and another offering up a framed poster of Snoopy proclaiming to be the sunshine of his life! Farmhouse sinks, penny tiles on the floor, and more of the shiplap found throughout the home give each bath a whimsical appeal, and guests will find it is impossible to be in a bad mood when performing their morning ablutions. 

The backyard offers up a private oasis that adds to the charm of Grayduck, providing a large, paved patio divided into seating, dining, and grilling sections, ensuring that the moments spent out here will be successfully fun! An outdoor shower will keep the sand outside where it belongs. 

Reserve Grayduck 207-C Today 

The adventures you will have exploring the nooks and corners of Cape Cod will be made even more special when you come home to the comforts of Grayduck every day of your stay! Contact us today!

The stunning landscape found on America’s favorite summer playground, Cape Cod, is the ideal spot for one of our more popular Pretty Picky Properties vacation sanctuaries, Cahoon Lagoon 036-B. Offering six beautiful bedrooms, nine baths, and a location at the tip of Long Pond that ensures the views will be so fantastic you will never want to leave, this Cape Cod vacation property features room for up to 14 guests. Bring along the cousins, the siblings, and your mother who has sacrificed so much to ensure you have everything, and plan for an escape to Cape Cod that you will cherish forever! Today, we want to shine the spotlight on this gorgeous home, helping build up the anticipation you will feel in the days, weeks, and months leading up to your vacation of a lifetime, so pour yourself a glass of your favorite beverage, slip out of your shoes, and relax in paradise for a few minutes of your very busy day in real life! 

Click here to book Cahoon Lagoon 036-B or keep reading for more info!

Traditional New England Cottage? 

Yes, the clapboard siding offers a traditional taste of New England life, but the size, beauty, and luxury of this expansive home is anything but ordinary! Featuring wood floors that lead the way to rooms filled with light and comfort, vaulted ceilings add grandeur, and comfortable furnishings will make you feel at home. A spacious kitchen with marble countertops and a center island contrasts beautifully with the forest green painted cabinets, and professional quality appliances in black steel will help you find your joy again while cooking. The dining room table is anchored under an iron chandelier, providing a farmhouse appeal to the room that will be the center of many family activities. The formal living room offers no television, but it’s cheerful fireplace and book-lined shelves make it the perfect conversation or reading area, and there are plenty of other televisions in Cahoon Lagoon if that is the entertainment you prefer! 

A game room with a pool table provides more ways to play, and three comfortable leather sofas offer a great place to watch the state-of-the-art television hanging on the wall opposite. An office with a desk, printer, and high-speed internet allows our hardworking guests to keep their hand in at work, but hopefully the entertainment options found in Cahoon Lagoon will keep you otherwise occupied! A ping pong table, multiple places to sit outside, a barbecue grill, a firepit in the backyard, and kayaks provided for our guests to use ensure that every minute of your stay is filled with fun and excitement. Views of Long Pond are stunning and serene. 

The Best Is Yet to Come 

The days you spend in Cahoon Lagoon will be some of the best you have ever experienced, and of course, Cape Cod is destined to be your favorite place to explore, but coming home every night to the comforts found in our bedroom retreats promises to bring you to the next level of contentment. King beds anchor four of the six bedrooms—plush, comfortable, and just waiting for you to slide between the high-end linens that top them and lose yourself in the sweet oblivion of a deep and peaceful sleep. The remaining two bedrooms are where the kids will laugh, play, and sleep in twin beds—three in one room, two in the other—and as the sun sets on another day in paradise, it’s the peace and serenity in this beautiful home that will bring the best memories. Soak away any stress you may be feeling in deep tubs with a glass of your favorite wine, a good book, and soft music in our spacious and spa-like bathrooms; as we mentioned earlier, there are nine of them in Cahoon Lagoon, something that will help limit morning traffic jams when everyone is trying to get ready at the same time! Fully equipped laundry rooms will be popular spaces, especially with those who are traveling with children. No matter how much clothing you pack in your bags, children always manage to go through more than you bring, so just pack light (saving room for souvenirs) and use the full-sized washer and dryer as often as you like. 

The Beauty of Cape Cod 

The beauty of Cape Cod is reflected in the décor of this stunning property, revealed in the artwork hanging on the walls, in the pieces lining the shelves, and in the views you will enjoy through every window. Reserve this beautiful escape today and enjoy a Cape Cod getaway that is both comfortable and exciting! Contact us today!

Everyone deserves the type of vacation that spoils from start to finish. Visiting an exotic destination, spending long days at the beach, and wonderfully long evenings living in the lap of luxury in a vacation home that could be described as a vacation experience! When your upcoming journey brings you to the historic charms and sandy beaches of Chatham on Cape Cod and you decide that now is the time for that vacation of your dreams, choosing our Pretty Picky Properties Shore Daze 096-C for your home sweet Cape Cod vacation home will make your dreams come true in every way! Offering 4 serene bedrooms, 3.5 updated and spa-like baths, and space enough for up to 10 travelers to live together in luxury and harmony, this beautiful house will become a home when you and your favorite traveling partners reside within! 

Click here to book Shore Daze 096-C or read on for more info!

Cheerful and Welcoming 

Offering a classic New England style with a sophisticated twist, the smile on your face will begin to bloom at your first glimpse of the clapboarded-sided home that you will call your own. Looking like something out of a fairy tale, this two-story home sits proudly on a lot filled with immaculately groomed landscaping and brings cheer in the form of colorful boxes of flowers flanking each of its front windows. Located just a short distance from the iconic Oyster Pond, a saltwater tidal pool fronted with sandy beaches and warm waters to swim in, and also offering a close proximity to the shops and restaurants of idyllic downtown Chatham, Shore Daze is a winner from day one. 

Step inside and follow the paths created by light, wide-planked wood flooring into spaces filled with light and warmth. Walls painted the soft gray of a dove’s wings provide the perfect complement to plank-lined ceilings painted in a glossy white, offering up the appearance of a classic beach cottage, only on a much larger scale. An open concept floor plan allows guests to stay connected as they do their own things: watching television from the plush depths of the sofa in the living room; playing board games at the long wood dining table that center the space; or foraging for snacks in the fully equipped kitchen space. High-end materials are a theme in this sumptuous home that provides elegance yet comforting appeal that will make you feel at home. The wood floors that we have already mentioned, high-end appliances, marble countertops, and an expansive center island with space for five barstools surrounding its footprint are just some of the extras that make Shore Daze shine bright. And because the surprise luxuries are a constant in this sweet escape, a sunroom with walls of windows looking out into the yard offers another place to eat, relax, or play a game of rummy with friends or family. 

Throughout the home, the sea is reflected in the décor, offering a cheerful bunch of tin fish swimming across the walls in one room, a tryptic diagram of another school of fish hanging above the king bed in the master suite, and walls the color of the sea on a sunny day in the second master suite located on the second floor. The bedrooms feature state-of-the-art televisions, helping ease the transition into dreamland, and the aforementioned upper-level master even offers a comfy sitting area where guests can enjoy their morning coffee while looking out over the landscape, perhaps catching glimpses of Oyster Pond from their quiet perch. Updated fixtures in sparkling clean baths, a fully equipped laundry room, and professional fitness equipment in the small cabana opposite the pool finish up the tour of the interior spaces of Shore Daze, but as you might expect, there are still some more surprises that await! 

The Backyard Oasis 

There’s a lot to do on Cape Cod, but don’t be surprised if you feel like spending much of your time in the backyard oasis of Shore Daze instead! Offering something quite rare in a Cape Cod home, the backyard is anchored by a crystal-clear heated swimming pool so it is always the perfect temperatures for a family pool party, but if you are feeling a little chilly, the hot tub located at the side of the home will warm you right up. Featuring an outdoor kitchen with a gas grill, multiple seating and dining areas, and a gas firepit surrounded by cushioned chairs, the resort feel of this beautiful escape will truly make you realize that you chose the right home in which to shelter during your Cape Cod adventures in Chatham. 

Reserve Shore Daze Today 

Standing out in a sea of normalcy, this special home will be an integral part of your vacation experience! Contact us today!