14 Winter Wonderland Airbnbs in New England We’re Booking Right This Second

Hot cocoa in hand at all times, of course

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winter wonderland airbnbs

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


Best A-Frame

The Canopy House

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Most Eco-Friendly

Berkshire Mountain Retreat

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Best Decor

Stylish Shales Brook Cottage

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Best Cabin

Cozy Stockbridge Cabin

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Best Woodland Escape

Warm Pine A-frame Nestled In The Trees

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winter wonderland airbnbs canopy

Best A-Frame

1. The Canopy House (Stowe, Vermont)


  • Why We Love It: hot tub, hair dryers, laundry, coffee maker, dishwasher
  • Sleeps: 8 (3 bedrooms, 4 beds; 2 baths) 
  • Nightly Rate: from $564
  • Standout Review: “One word: perfection. This Airbnb was well thought out and very homey. It was close to everything we wanted to do and had every amenity we needed. The hot tub was lovely, the views were excellent and the beds were comfortable.”

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.

winter wonderland airbnbs berkshires mtn retreat

Most Eco-Friendly

2. Berkshire Mountain Retreat (Lee, Massachusetts)


  • Why We Love It: fire pit, indoor fireplace, soaking tub, laundry, eco-friendly energy sufficient
  • Sleeps: 8 (3 bedrooms. 4 beds; 2 baths)
  • Nightly Rate: from $298
  • Standout Review: “This sun drenched, peaceful, airy home in the [B]erkshires was a wonderful getaway from the city. It’s perfectly located between Lenox, Lee, and Stockbridge. We had so much fun exploring all these cute little towns with great restaurant choices, in addition to being close to Monument Mountain and Pleasant Valley for hiking. The home itself is modern yet cozy, with everything needed for a short or long stay.”

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). 

winter wonderland airbnbs stylish shales

Best Decor

3. Stylish Shales Brook Cottage (Becket, Massachusetts)


  • Why We Love It: children’s toys, books, record player, fireplace, laundry  
  • Sleeps: 4 (2 bedrooms, 2 beds; 1 bath)
  • Nightly Rate: from $213
  • Standout Review: “We had a great time at this place. Well-designed, clean, and comfortable, in the middle of beautiful nature. Everything is considered for guests, including kitchen utensils. Highly recommended.” 

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).

winter wonderland airbnbs stockbridge cabin

Best Cabin

4. Cozy Stockbridge Cabin (Stockbridge, Massachusetts)


  • Why We Love It: fireplace, record player, books, children’s toys and decor
  • Sleeps: 6 (3 bedrooms, 5 beds; 1.5 baths) 
  • Nightly Rate: from $292
  • Standout Review: “Fabulous cabin in the Berkshires! Great location by Stockbridge Bowl and the picturesque surrounding villages. The house has everything a family needs. Wish we could have stayed longer!”

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…

winter wonderland airbnbs warm pine a frame

Best Woodland Escape

5. Warm Pine A-frame Nestled In The Trees (Center Conway, New Hampshire)


  • Why We Love It: VHS collection, board game, deck, fireplace
  • Sleeps: 4 (2 bedrooms, 3 beds; 1 bath) 
  • Nightly Rate: from $163
  • Standout Review: “This was the perfect private getaway that we needed. We were so happy to be close to town and yet feel like we were alone in the woods.” 

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.

winter wonderland airbnbs skyline

Best Amenities

6. Skyline Cabin (Sunderland, Vermont)


  • Why We Love It: hot tub, pet-friendly, fire pit, soaking tub, games
  • Sleeps: 6 (3 bedrooms, 3 beds; 3 baths) 
  • Nightly Rate: from $564
  • Standout Review: “We loved our stay at Skyline Cabin. It is beautifully and simply appointed. Tasteful, no clutter and had everything we needed. Incredible views, private, spacious, and looks just like the photos-perhaps even better. Wonderful hosts who were very communicative. A 5 star rating to be sure.”

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. 

winter wonderland airbnbs oceanfront escape

Best Big Group Getaway

7. An Oceanfront Escape in Coastal Maine (Kennebunk, Maine)


  • Why We Love It: games, outdoor furniture, expansive porch, soaking tub, fireplace 
  • Sleeps: 16 (7 bedrooms, 13 beds; 4.5 baths) 
  • Nightly Rate: from $693
  • Standout Review: “This is the perfect holiday home for our group of friends with kids. The house is beautiful, very comfortable and the view of the water. The owners are responsive and very kind. There is nothing missing at the house and everything is nearby. We look forward to returning.”

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.

winter wonderland airbnbs treehouse

Best Treehouse

8. Heavenly Treehouse in the Countryside (Willington, Connecticut)


  • Why We Love It: fire pit, board games, free coffee and tea, fireplace
  • Sleeps: 4 (1 bedroom, 2 beds; 1 bath)
  • Nightly Rate: from $228
  • Standout Review: “This was my second stay at the treehouse and I've already booked my third. It's the most cozy, peaceful and beautiful location. The treehouse is clean, warm and just so cool! It's slightly rustic but also really functional. The near by hiking trails are endless and farm animals you can literally watch all day from the treehouse.”

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.

winter wonderland airbnbs ross house

Most Modern

9. Ross House (Block Island, Rhode Island)


  • Why We Love It: pet-friendly, laundry, coffee maker, roof deck, fireplace, 25-foot-high ceilings, modern
  • Sleeps: 7 (2 bedrooms, 4 beds; 2.5 baths)
  • Nightly Rate: from $1,557
  • Standout Review: “The house was minimal and spectacular, but also comfortable. The setting is perfect. The sun rises over the water off the large well appointed kitchen deck. My guests loved the bedrooms and bathrooms but as everyone mentions the outdoor shower was superlative.”

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.”

winter wonderland airbnbs quonset

Most Unique

10. The Quonset (Tiverton, Rhode Island)


  • Why We Love It: hot tub, games, fire pit, children’s toys, pet-friendly, fully stocked pantry, unique design
  • Sleeps: 8 (4 bedrooms, 7 beds; 2 baths)
  • Nightly Rate: from $544
  • Standout Review: “Loved staying at The Quonset Hut by Sharon…there were 6 of us total for a writers’ retreat. Plenty of space to spread out as well as gather and commune! The vibe was ‘effortless cool,’ and I felt like I was on a true vacation away from the typical hum-drum, cluttered existence at home. We cooked, we swam, we jogged, we watched the deer and bunnies and hedgehogs. Would stay again. Rain showers a plus!”

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. 

winter wonderland airbnbs mad moose

Best Deal

11. Mad Moose Lodge (Stoneham, Maine)


  • Why We Love It: pet-friendly, game room, soaking tub, outdoor deck
  • Sleeps: 6 (2 bedrooms, 4 beds; 2.5 baths)
  • Nightly Rate: from $251
  • Standout Review: “Mad Moose Lodge was a fantastic getaway from our busy city life. The house was stunning and very well maintained with exquisite views of the woods and mountains behind you.” 

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.

winter wonderland airbnbs coastal cottage

Best for Exploring Newport

12. Serene Coastal Country Cottage (Middletown, Rhode Island)


  • Why We Love It: toiletries, soaking tub, hot tub, fireplace
  • Sleeps: 8 (3 bedrooms, 6 beds; 1.5 baths)
  • Nightly Rate: from $405
  • Standout Review: “We loved staying here. The home was well equipped and very comfortable. We were here for a family wedding in Newport and it was as a good location. Loved the comfortable backyard!”

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.”

winter wonderland airbnbs tiny home

Best Tiny Home

13. Luxury Tiny Home (East Lyme, Connecticut)


  • Why We Love It: fire pit, pet-friendly, toiletries, games, children’s toys 
  • Sleeps: 4 (1 bedroom, 2 beds; 1 bath)
  • Nightly Rate: from $177
  • Standout Review: “If you are reading this, just book this amazing Airbnb. Every little detail is perfectly thought out and the space couldn’t be more perfect.”

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.

winter wonderland airbnbs mountain view lodge

Best for Skiing

14. Mountain View Lodge (Dover, Vermont)


  • Why We Love It: fire pit, fireplace, games, hot tub, pet-friendly, toiletries  
  • Sleeps: 16 (8 bedrooms, 10 beds; 4 baths)
  • Nightly Rate: from $500
  • Standout Review:

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.

purewow author

Freelance Writer

Lauren Dana Ellman is a New York-based freelance writer and editor. As a self-proclaimed shopaholic, she is most often found wandering through Home Goods, scrolling through...