14 Winter Wonderland Airbnbs in New England We’re Booking Right This Second
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New England makes for a charming year-round vacation destination, but come winter, the region becomes even more enchanting. (Think: picturesque small towns covered in a blanket of fresh snow and decked out in holiday decor: How dreamy?!) So, if you haven’t experienced the joys of winter in New England—IYKYK, and if you don’t, you definitely should—now’s the perfect time. Book a big group weekend at this oceanfront home in Kennebunk Maine that sleeps 16. Go skiing in the mountains of Vermont and then get your après on at the Mountain View Lodge in Dover. Write that novel in an off-the-grid lair as you cozy up by the fireplace. we’ve handpicked the area’s most incredible Airbnbs that feel like real-life winter wonderlands. Keep scrolling to check out these hidden gems, and be sure to book yours, STAT.
Winter Wonderland Airbnbs at a Glance
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10 Small Town Winter Wonderlands in the U.S.
1. The Canopy House (Stowe, Vermont)
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Airbnb
Stowe is known for its abundance of winter sports (skiing and snowboarding are both popular here), and this ethereal Airbnb is the best place to stay when in town. Watch the snowfall and sip on a mug full of hot cocoa from the comfy couch in the greenery-filled main living room, which offers lots of natural light plus a sleek white fireplace, which only enhances the cozy vibe. Or, venture outside for a soak in the hot tub followed by some stargazing.
2. Berkshire Mountain Retreat (Lee, Massachusetts)
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For a fun—and easy!—group getaway in the middle of winter, head to The Berkshires. Just two hours from Boston, this dynamic destination is teeming with charming Hallmark-esque towns like Lee. After a day spent exploring and shopping in town, check into the Berkshire Mountain Retreat, where you can relax by the fireplace, take a dip in the deep soaking tub (bonus points if you add a glass of vino) or roast s’mores around the fire pit. The spacious, sun-drenched kitchen is ideal for cooking hearty, warm comfort meals (it is soup season, after all).
3. Stylish Shales Brook Cottage (Becket, Massachusetts)
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From the outside, this two-bedroom cottage in the Berkshires looks pretty ordinary; however, one step inside, and you’ll feel like you’ve been transported to your cool, artsy friend’s vacation home. The recently renovated interiors feature fun pops of green, a wood-burning stove, a fireplace and funky bedrooms with striking patterned wallpaper. The property is located in Beckett, putting you within close proximity of festive Christmas events in nearby Stockbridge (which hosts concerts, markets and more) and Pittsfield (don’t miss the local Christmas market).
4. Cozy Stockbridge Cabin (Stockbridge, Massachusetts)
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airbnb
As previously mentioned, the quaint town of Stockbridge comes alive at Christmastime, when Main Street is decorated in festive wreaths, lights and even vintage automobiles. This cabin puts you close to all the holiday cheer—though I totally wouldn’t blame you if you just stayed put here all weekend long. (This is a no-judgment zone, FWIW.) The home’s rustic-chic wooden interiors—complete with a stunning stone fireplace—set the picture-perfect scene for a laid-back, long-weekend escape. Snuggle up with one of the throw blankets and watch the snow fall from the skylight with a book and a record playing softly in the background. Relaxation awaits…
5. Warm Pine A-frame Nestled In The Trees (Center Conway, New Hampshire)
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airbnb
This adorable A-frame is just a few miles away from the village of North Conway and hiking and skiing trails over at White Mountain. Here, though, there is nothing to do but unwind while surrounded by towering pines. Throw on your warmest winter coat and head to the expansive deck—be sure to bring your phone to snap some ‘grams—before warming up inside under the down comforter. The nostalgia-inducing VHS collection and board games are great for a chill night with friends.
6. Skyline Cabin (Sunderland, Vermont)
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Situated in the heart of Vermont’s Green Mountains, a stay at Skyline Cabin is a dreamy winter getaway for the books. While the Airbnb’s tranquil surroundings are well worth the trip here alone, it’s the amenities that really make it a stand-out pick. When you’re not hanging by the wood-burning fireplace or relaxing in the deep soaking tub, guests can venture outside to the fire pit, outdoor hot tub, or one of the Adirondack chairs. Alternatively, warm up indoors: The game room in the basement is stocked with a ping-pong table, board games and video games to keep everyone in your group entertained for hours on end.
7. An Oceanfront Escape in Coastal Maine (Kennebunk, Maine)
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While it’s best known as a popular summer destination, Kennebunk is chock-full of holiday cheer: Don’t miss the annual Christmas Prelude or the Holiday Trail of Lights! Besides—and, brace yourselves, people: I’m pulling a T. Swift here—few things are as beautiful as snow on the beach in winter. That’s why this sprawling oceanfront home makes for an idyllic escape—even if it is too chilly to go in the water. Spanning 3,500 square feet, this property offers plenty of room to lounge, and it’s even decked out in beautiful blue-hued beachy decor that’s worthy of its own magazine spread. Guests can sip coffee on the porch and play ping-pong or board games (a little healthy competition never hurt anybody). We’d also be remiss not to call out the picture windows in the sitting room, which offer exceptional beach views.
8. Heavenly Treehouse in the Countryside (Willington, Connecticut)
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Live out your childhood dreams by booking this real-life treehouse, which makes for an uber-romantic winter weekend escape. When the surrounding trees are covered in fresh powder, you’ll feel like you’re living in a real-life snow globe. Take a hike (literally!) along the 40-acre grounds and head out to explore the nearby wineries and breweries before retreating to the outdoor fire pit, where stargazing opps abound. Best of all, there are adorable farm animals on-site, including sheep, goats, chickens and pigs. One guest described their stay here as “absolutely magical,” while another deemed it “An absolute dream” and “a sweet escape for our little family.” However, this is a legit treehouse, so expect a rustic stay.
9. Ross House (Block Island, Rhode Island)
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airbnb
This season, hunker down at this uber-modern Airbnb perched atop the 200-foot-tall Mohegan Bluffs on Block Island. This small isle is essentially crowd-free come cold-weather season, and, as such, it’ll feel like your own private oasis. Airbnb highlights include 270-degree ocean vistas, tons of natural light, 25-foot-heigh ceilings and expansive windows. However, for the best views of the snowy shoreline, you’ll want to head up to the rooftop deck—just be sure to bundle up! One guest wrote, “Ross House is a beautiful, contemporary home overlooking the Atlantic Ocean, perfect for disconnecting from the distractions of everyday life.”
10. The Quonset (Tiverton, Rhode Island)
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airbnb
The Quonset dates back to the 1940s, but it’s since been renovated. Today, it’s filled with fun treasures, including a hidden kids’ room, lots of games and a one-of-a-kind baby grand piano. We’d also be remiss not to mention the brand-new hot tub, plus a fully stocked pantry for endless snack options. Meanwhile, the industrial-inspired interiors offer vibrant pops of green—from the couches to the cabinets, to the actual house plants— which only adds to the ‘gram-worthy aesthetic. Lastly, keep in mind that the Airbnb is just a half-hour from Newport, where visitors can tour extravagant Gilded Age mansions complete with over-the-top holiday decor, check out craft fairs, attend concerts and admire the twinkling holiday lights.
11. Mad Moose Lodge (Stoneham, Maine)
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Winter sports enthusiasts will especially appreciate a stay at Mad Moose Lodge, which offers easy access to skiing and snowshoeing in the nearby mountains. However, it’s entirely possible you may not even want to step foot outside your rustic-inspired bedrooms—outfitted with wooden four-poster beds, black-and-red checkered blankets and printed rugs—except to take a refreshing bath, play pool or sip (spiked) hot chocolate al fresco.
12. Serene Coastal Country Cottage (Middletown, Rhode Island)
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airbnb
This serene coastal cottage in Rhode Island makes a great home base for exploring nearby Newport, which, as previously mentioned, goes all-out for the holidays. The coastal grandmother-esque living room area—complete with a wood-burning fireplace—is excellent for warming up with a hot drink, while the expansive outdoor area features a hot tub and gorgeous gardens. Also, the tub here is ideally situated adjacent to the window, so you can soak up views of the surrounding lush greenery (see what I did there?). One guest described the home as “absolutely beautiful,” adding, “It’s well decorated, well stocked with kitchenware, and very spacious. We had a large group in town for a wedding and we all fit really comfortably. The hot tub was an added bonus! Super clean and relaxing.”
13. Luxury Tiny Home (East Lyme, Connecticut)
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What this tiny home lacks in size, it certainly makes up for in charm. The sleek interiors feature contemporary decor and fun touches like heated bathroom floors and Amazon Alexa-controlled shades (read: no need to get out of bed to shut the blinds!). After exploring nearby downtown Niantic—which hosts festive-themed events all throughout the holiday season, including parades, 5Ks and holiday strolls—head to the home for a game of giant Connect Four or cornhole out on the deck.
14. Mountain View Lodge (Dover, Vermont)
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The four-acre Mountain View Lodge is just two minutes from Mount Snow, which attracts visitors from across New England (and beyond) for its prime skiing opps. However, non-skiers can hang out at this home to take advantage of a full range of A-plus amenities, including a hot tub for soaking, a fire pit for keeping warm and a fireplace where you can sit in front of while doing, ahem, absolutely nothing. You can, however, take in the postcard-worthy vistas from almost anywhere in the home thanks to its many floor-to-ceiling windows.
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