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Chalet vacation rentals in Windham County

Find and book unique chalets on Airbnb

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Popular amenities for Windham County chalet rentals

Family-friendly chalet rentals

Guest favorite
Chalet in Peru
4.9 out of 5 average rating, 63 reviews

Getaway in Green Mountains

AndrewRating, 5 stars2 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
Chalet in Winhall
4.8 out of 5 average rating, 75 reviews

Beautiful chalet for any season

ElizabethRating, 5 stars3 months ago
Convenient distance to Bromley. It was clean, comfortable, quiet. We felt right at home. Loved relaxing after skiing, watching some television in front of a nice fire! Would certainly want to stay there again!
Guest favorite
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars1 month 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, 445 reviews

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

OscarRating, 5 stars2 days ago
Beautiful place, real quaint and nice to stay at. The surroundings were real nice at nice and the nature was very nice to be surrounded by. All the amenities worked as expected and the beds were comfortable. The porch was our favorite place to relax at; hammock, yard, stereo playing from inside. Great stay … thanks Jason and Sara :))))
Superhost
Chalet in Wilmington
4.57 out of 5 average rating, 91 reviews

Cozy House - Mount Snow, VT

VincyRating, 5 stars3 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!
Chalet in Winhall
4.73 out of 5 average rating, 51 reviews

Valley Chalet minutes to Manchester, restaurants

GailRating, 5 stars32 months ago
The house is always clean and very comfortable, with nice amenities that are helpful in a house like having some oil and spices in the pantry, fans for the bedrooms, plenty of towels, etc. We always feel right at home while we're there. We made use of the streaming services like Disney+ for our kiddos, too!
Chalet in Peru
4.84 out of 5 average rating, 44 reviews

Vermont Mt. House, near Bromley and Hapgood Beach

EdwardRating, 5 stars3 months ago
Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.
Chalet in Jamaica
4.81 out of 5 average rating, 62 reviews

Stratton Mountain and Mount Snow 5 Bdrm Ski House

LucindaRating, 5 stars1 month ago
Nicholas’ place was just what we were looking for: pet friendly, near the ski areas and Jamaica State Park, within easy reach of Manchester, Newfane and Brattleboro, and proximate to our extended family. It was perfect. Although we were there in the snowy months, I can also see how the outdoor area by the fire pit would be an amazing place to enjoy in the evenings!

Luxury chalet rentals

Guest favorite
Chalet in Dover
4.98 out of 5 average rating, 63 reviews

A quintessential Vermont getaway

LauraRating, 5 stars2 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 favorite
Chalet in West Dover
4.98 out of 5 average rating, 50 reviews

Charming Chalet w. Hot Tub - 1 Mile to Mt. Snow

LaurenRating, 5 stars2 weeks ago
A beautiful spot perched amongst the trees and snowy woods. Cosy couches and fireplaces, a magical hot tub and generous touches, like extra wood, coffee and shampoo. I took my boys skiing nearby and we all loved every minute. Wouldn't hesitate to stay again
Guest favorite
Chalet in Dover
4.93 out of 5 average rating, 44 reviews

New! Custom Chalet minutes from Mt Snow w/ Hottub

ZacharyRating, 5 stars2 months ago
The house was fantastic. Great condition, cool layout! There was a ton of snow, and the property was well plowed, shoveled and sanded!
Guest favorite
Chalet in Winhall
4.89 out of 5 average rating, 79 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

LuisRating, 5 stars1 month ago
The property was spacious, clean, and well-equipped to accommodate our large group comfortably. Perfect for relaxing after a day on the slopes. The location was ideal, just a couple minutes drive from the ski resort. Bobby, the host, was incredibly responsive and helpful!. We couldn't have asked for a better place for our ski weekend and would highly recommend it to anyone looking for a great group getaway!
Guest favorite
Chalet in Wardsboro
4.88 out of 5 average rating, 42 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

KellyRating, 5 stars1 month ago
We really enjoyed our stay! The house is beautiful and perfect location for skiing at Mt snow or Stratton. Indoor hot tub was a huge hit & spacious living spaces were great for spending quality time together!
Superhost
Chalet in Dover
4.81 out of 5 average rating, 58 reviews

Spacious Vermont Chalet for Group Getaways

AnnaRating, 5 stars2 months ago
We stayed here with a large group when a lot of snow was falling! The Horst was very communicative about when the plow was coming etc. when we got there the hot tub needed some more water and treatment and they came the next day to fix it all up! It’s tucked away and felt private. We loved the fire pit area outside with snow falling around us as well as the indoor fire place! It was cozy and just as advertised! We enjoyed our stay here and would come back again.
Top guest favorite
Chalet in Winhall
4.98 out of 5 average rating, 98 reviews

Mountain view chalet with hot tub & fire pit!

JaymeRating, 5 stars2 weeks ago
Breathtaking views and 5 Star Host! My husband and I wanted to give our son and his friends a remote trip to Vermont. Ryan, our host, was so helpful and went above and beyond to make my son’s 18th birthday “guy’s trip” a success. We truly felt right at home and every single picture looks exactly like the property. Thank you Ryan-you’ve set a high bar.
Top guest favorite
Chalet in Wilmington
5 out of 5 average rating, 93 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

AmyRating, 5 stars1 week ago
We loved the Snow Chalet!! Such beautiful surroundings and well appointed. The beds were super comfy and the black out shades were great for the kids. Location was great and close to the grocery stories. Wilmington is a sweet town too with lots of cool shops. The club house pool was warm and the pool was nice and toasty. An awesome trip!

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