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Chalet holiday rentals in Windham County

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Windham County

Family-friendly chalet rentals

Superhost
Chalet in Peru
4.88 out of 5 average rating, 64 reviews

Getaway in Green Mountains

AndrewRating, 5 stars3 months ago
We stayed here with another couple and their dog two years back and had a wonderful time. I am so grateful that we came back this year with our dog, Chili, and she had the absolute best time! Old Manchester rd is really quiet and is great for off leash walks. Chili loved frequently seeing the other neighbors and their dogs (who were all friendly) on her walks. We’re also runners and so the road is great for running (mostly flat, minimal traffic, frequently plowed, amazing views of Bromley). Jennifer and Dan are both very friendly too. Jennifer did a good job of reaching out to us often making sure we had what we needed. Dan often came by to plow the driveway which was really nice too. Our last day was during a snow storm and they were flexible with checkout which was really helpful. This place really has everything you need and the location is excellent (close to Stratton, Manchester which has a dog park, and downtown Peru which has an outdoor ice skating rink
Guest favourite
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars3 months ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 453 reviews

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK

JasonRating, 5 stars1 week ago
The chalet is secluded, quiet and peaceful. We appreciated its location in the woodland, right near a stream. It was comfortable for our family and we would return again in the future.
Superhost
Chalet in Jamaica
4.86 out of 5 average rating, 94 reviews

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

DanielRating, 5 stars2 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
Superhost
Chalet in Wilmington
4.57 out of 5 average rating, 91 reviews

Cozy House - Mount Snow, VT

VincyRating, 5 stars4 months ago
Mariah’s cabin was perfect for our getaway. Lots of natural light, clean and had everything we needed. It was a quick drive to Mt Snow and close to some cute restaurants in Wilmington. I was given clear and very lengthy instructions for check in/check out and Mariah was responsive to some minor questions we had throughout our stay. I missed the opportunity to book the hot tub/clubhouse when we first made the reservation. Hoping future guests don’t make the same mistake and be sure to request it at the time of booking!
Top guest favourite
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Chalet in Peru
4.84 out of 5 average rating, 44 reviews

Vermont House, near Bromley Park and Hapgood Beach

EdwardRating, 5 stars5 months ago
Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.
Guest favourite
Chalet in Peru
4.85 out of 5 average rating, 89 reviews

Bromley Aframe - King Master Bed, Wood Fireplace

SamanthaRating, 5 stars1 month ago
All around a wonderful experience. Michael was lovely, super responsive and went out of his way to make sure we were comfortable. The house and amenities are well appointed. Bed was super comfy. Would absolutely stay again.

Luxury chalet rentals

Guest favourite
Chalet in Dover
5 out of 5 average rating, 48 reviews

Authentic Vermont Chalet: Year Round Vacation Home

ChristinaRating, 5 stars3 months ago
Beautiful spot with a cozy yet spacious house. Instructions were very clear on how to get in and the different features of the house. Perfect for a relaxing get-away with friends!
Top guest favourite
Chalet in Wilmington
5 out of 5 average rating, 62 reviews

Beautiful Home on 22 Acres w/Ponds & Central A/C

Christopher WRating, 5 stars1 month ago
Beautiful place. The house, the land. My family of 5 and our dog loved it. The kids loved the ponds and the games room. Vanessa was a great host and helped make it a great experience from start to finish. Cheers!
Top guest favourite
Chalet in Dover
5 out of 5 average rating, 35 reviews

Charming Mountain Chalet w/ Spa near Mt Snow

Caitlin Rating, 5 stars2 months ago
Lovely stay in a cozy, comfortable house only 15 minutes from Mount Snow. We enjoyed post ski-day nights by the fire, with plenty of comfortable seating and board games galore. The yard was great for our dogs and features like the koi pond and hot tub were easy to enjoy in a peaceful and private environment. We’ll be back!
Guest favourite
Chalet in Dover
4.98 out of 5 average rating, 63 reviews

A quintessential Vermont getaway

LauraRating, 5 stars3 months ago
Linda was awesome! She was super responsive and helpful. We ran into several snags with our trip due to weather but we kept in constant communication and it all worked out. The house is cute and has a certain charm to it. The hot tub wasn't working but that was communicated to us a day before so we were aware. The bathrooms are a bit small, particularly the showers. Overall we had a great trip. Very close to Mt Snow. Quiet and scenic location. Fireplace was nice to have. We replenished with kindling and dry wood just so we could keep a nice warm fire going. Lovely host & lovely home.
Guest favourite
Chalet in Winhall
4.89 out of 5 average rating, 80 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

LukeRating, 5 stars1 month ago
We had a wonderful weekend at The Barn. Truly a comfortable and scenic space for us to relax and enjoy the weekend. Host was very responsive and everything worked as we expected. A great choice for a weekend away with a large group of friends easily accomodated.
Superhost
Chalet in Dover
4.65 out of 5 average rating, 31 reviews

Mount Snow Chalet w/ Ski-Home Trail & Indoor Sauna

CarolRating, 5 stars4 months ago
The house was super close to the mountain The house had everything you could possibly need in the kitchen Three living rooms which was nice we were unable to turn the sauna on sadly Perfect ski house entrance with a lot of room the take everything off without tracking into the rest of the house Large table to eat and play games on I would definitely stay here again
Guest favourite
Chalet in Wardsboro
4.89 out of 5 average rating, 44 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

ZackRating, 5 stars1 month ago
absolutely gorgeous place with a beautiful veiw as stated i wpuld 10/10 stay again highly recommended property for familes or friends always responded well too
Guest favourite
Chalet in Dover
4.9 out of 5 average rating, 40 reviews

Hot Tub-TheaterRm-Game Room-FirePit-1mi To Mt Snow

TedRating, 5 stars2 weeks ago
Nice amenities. Bit smaller than expected from the photos but everything is as advertised.

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