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Holiday Homes on the Cape and Islands

Josie Cataldo | 12/5/2022 (updated 11/30/2023)
It's officially the most wonderful time of the year, and we can't think of a better place to spend this special season than on the Cape and Islands! Celebrate this most magical time in the WeNeedaVacation vacation rental of your dream.

Sandcastle by the Sea

Looking to trade in snow for sand but still want to spend “the most wonderful time of the year” in New England? If so, Sandcastle by the Sea is the perfect place for you. Cozy up with a cup hot cocoa and seek shelter from the rhythmic, roaring waves right outside your window. Sculpt your own sandcastle out of gingerbread, frosting, and pinwheel peppermints. Warm up with some sugar cookie cocktails that you concocted at your very own bar. Fall asleep to the soundtrack of the sea and wake up to the winter sun streaming through the wall of windows. Sandcastle by the Sea is perfect for those of you who are tempted to head to the tropics for the holidays but can’t seem to tear yourself away from the frigid temperatures that signify Santa’s arrival.

Modern Marvel in Woods Hole

When you book a stay at the Modern Marvel in Woods Hole, prepare to feel like you’re spending the holiday season in the coastal California home of your dreams. This property is fit for the films, worthy to be the backdrop for Hollywood’s next holiday movie. Situated just minutes away from Nobska Beach, this tranquil oasis is the perfect place for you to indulge in lavish living like the main character you are. Relax in a room filled with records and choose the track that’ll define your Christmas Cape escape for years to come. Scale the ship ladder up to the roof deck and make your Christmas wish on a shooting star. Wake up in your light-filled bedroom and strut down the “catwalk” to the kitchen for a cup of cocoa. Modern Marvel is meant for those of you looking to treat yourself to a West Coast winter wonderland without having to give up your dream of a Cape Cod Christmas.

The Owl's Nest

Welcome to the “Owl’s Nest,” a picturesque post and beam retreat located steps away from Sandy Neck beach. The interior of this home is enthralling, it’s as whimsical and unique as the snowflakes that fall from the New England sky. Each element of this home is welcoming & warm, the touches of green that incorporate Christmas cheer, the impeccable pine floors, and the simple yet alluring artwork. Climb your way up to the third-floor loft and feel like a snow bird seeking shelter in your nest. This home is your safe haven from the bitter chill that rolls in with the swift sea breeze. Relax and unwind by the fireplace with a piping hot cup of tea and your latest winter beach read. Let the dialogue of Elf be background music as you cook your comfort meal in the kitchen of your dreams. The charm of Owl’s Nest is undeniable, and the inclination to want to stay in this idyllic environment forever is overwhelming.

Nestled in Wellfleet's Wilderness

Spend this holiday season relaxing and unwinding in this whimsical Wellfleet home nestled in the National Seashore. This serene sanctuary is the perfect place to escape for a holiday reset and enjoy the beauty of the Outer Cape and all it has to offer. Let yourself doze off to the sounds of birds dancing in the treetops and ducks diving for their dinner in Higgins Pond. Spend your evenings bundled up on the back deck stargazing, seeing who can spot a shooting star first. Wake up to first light streaming in through your windows and watch the remnants of the sunrise's colorful sky reflect on the crystal clear surface of the pond. This home enveloped by Wellfleet's wildlife is a true gem and an ideal destination for anyone looking to escape from the chaos of the holiday season.

The Rolling Hills of Quidnet

Situated on acres of rolling hills draped with a blanket of glimmering snow during the wintertime, let this Nantucket home be your haven for the holidays. Cozy up by the fireplace and listen to Christmas classics as the snow falls outside your window. Go for a winter wonderland walk at Squam Farm, an enchanting nature reserve just steps away from your sanctuary. Cook your favorite comfort meal in your very own gourmet kitchen and enjoy the fruits of your labor beneath the warm glow of the chandelier. After fading willingly into a food-induced coma, relax with a good book in the luxurious living room. This Nantucket oasis combines old farmhouse charm, luxury amenities, and an impressive amount of acreage. It's the perfect place for you to embrace the beauty and serenity of Nantucket Island during the off-season.

Akwaaba Manor

What better way to celebrate the holidays than in your very own gingerbread house on the idyllic island of Martha’s Vineyard? Live out your candy land fantasy at the magnificent Akwaaba Manor. The exotic exterior of this home resembles the color of your favorite flavor of cotton candy, blue raspberry. Your sweet tooth will be summoned, and before you know it, you’ll be creating the most magnificent gingerbread village Martha’s Vineyard has ever seen. Your delicious Christmas display is the star of the show beneath the crystal chandelier that spotlights the extravagant dining room table. All the hard work from crafting that sugary sweet Christmas village earns you a soak in the luxurious clawfoot tub. Your gingerbread daze has you ending the night on one of the comfy couches, surrounded by friends and family who have just engaged in quite the competitive round of Scrabble. Your dreams of staying in a life-size gingerbread house have come true, and your sweet escape to the Island of Martha's Vineyard will become a holiday tradition for years to come.