Chalet vacation rentals in Windham County

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Top-rated chalet rentals in Windham County

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Guest favorite

Chalet in Dover

4.98 out of 5 average rating, 94 reviews

Mountain Chalet: brook-hot tub-firepit-mins to ski

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow and Stratton, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best cuisine VT has to offer.

Guest favorite

Chalet in Dover

4.94 out of 5 average rating, 116 reviews

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

My super cozy mountain chalet 10 mins from Mount Snow is the perfect spot to host your Vermont vacation! Let the grownups cozy up by the wood-burning fireplace in the living room, while the kids hang out in the second living room and game room downstairs. With air hockey, shuffleboard, and poker table, they’ll be busy for hours. Hmmm….maybe the grownups will claim that space for themselves! After a long day on the slopes or trails, the sauna, hot tub, or jacuzzi tub will feel great on tired musc

Guest favorite

Chalet in Stratton

4.99 out of 5 average rating, 159 reviews

Chalet Near Ski, Hike, Swim & Golf W/Disc Golf!

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

Guest favorite

Chalet in Wardsboro

4.94 out of 5 average rating, 31 reviews

Maple Brook Chalet w/ Indoor Hot Tub, Firepit, EV

Relax in front of the fireplace with the whole family, soak in the indoor hot tub, roast marshmallows over the outdoor fire pit or grill up some bbq at our spacious chalet after a day of hiking, exploring or skiing in southern Vermont. Nestled between Mt Snow and Stratton Ski Resorts, we’re just a short drive from local farms, snow mobile trails, boating, sledding, hiking and horseback riding. With lots of family friendly restaurants in the area boasting local flavors, you’ll never go hungry!

Guest favorite

Chalet in Wilmington

4.95 out of 5 average rating, 131 reviews

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

Guest favorite

Chalet in Londonderry

4.93 out of 5 average rating, 100 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Guest favorite

Chalet in Dover

4.92 out of 5 average rating, 287 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Superhost

Chalet in Dover

4.86 out of 5 average rating, 232 reviews

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Guest favorite

Chalet in Jamaica

4.83 out of 5 average rating, 167 reviews

Artists Chalet minutes from Stratton Ski Resort

One of a kind, brand new, hand built by owners in the heart of the Green Mountains. House boasts spacious high ceilings, built with wood from the property and custom windows that reflect the true intention of the h’om’e. Beautiful pikes falls less than one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Partial mountain view’s! During the winter season, all wheel drive or 4WD is recommended. Pets are welcome on a case by case basis and may be subject to a Pet Fee.

Guest favorite

Chalet in Dover

4.94 out of 5 average rating, 103 reviews

8Min to MtSnow, HotTub, FirePit, GameRoom, Dogs Ok

✔ 8 Minutes to Mount Snow, 30min To Stratton, 60min to Okemo ✔ 4 Bedrooms, 3 Bathrooms, Sleeps 10 comfortably ✔ Hot Tub Under Pergola & String Lights ✔ String-Lit Fire Pit Area w/ Adirondack Charis ✔ Game Room With Air Hockey & Ring Toss ✔ Dog-Friendly ✔ Lake Whitingham/Harriman Reservoir is 20 minutes away to enjoy boating & fishing ✔ Fast Wifi For Remote Working & Streaming ✔ Quiet, Peaceful, & Private ✔ High Chair, Pack N' Play Provided ✔ All Linens/Towels/Soaps Provided

Guest favorite

Chalet in Jamaica

4.98 out of 5 average rating, 241 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, screened-in porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hike, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Guest favorite

Chalet in Dover

4.94 out of 5 average rating, 113 reviews

Mountain Chalet mins from Mt Snow Skiing/hiking

Experience nature at this peaceful mountain retreat. World class skiing at Mt Snow is just 14 minutes away. After a day of outdoor activities enjoy a relaxing time in front of the fireplace. This cozy chalet boasts exposed wood beams and wood paneling all throughout the house. You will wake up in the master bedroom with views of the woods. During the off winter months, enjoy your morning coffee on patio with views of the mountain. The kitchen is well equipped with your cooking needs.