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Chalet holiday rentals in Bennington County

Find and book unique chalets on Airbnb

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Popular amenities for Bennington County chalet rentals

Family-friendly chalet rentals

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

Getaway in Green Mountains

AndrewRating, 5 stars4 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 Manchester Center
4.84 out of 5 average rating, 109 reviews

Private forest retreat near town, AT/LT trails

ConnorRating, 5 stars4 months ago
Well worth the stay! Thinking of doing it all again next year. Home was clean and ready when we arrived, heat and amenities all worked - zero complaints.
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 stars2 weeks 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 stars3 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 stars5 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.

Luxury chalet rentals

Superhost
Chalet in Winhall
5 out of 5 average rating, 9 reviews

4+BR pet-friendly w/ hot tub & Stratton parking!

YairRating, 5 stars4 months ago
Great house, as described. Very responsive host before and during the stay with clear instructions. The couple of things that stood out: 1. Big house; easily sleeps 10, can get a couple more kids in if you want. 2. 15 minutes to Stratton with a parking permit provided which was key. 3. Indoor garage space was great, especially as it was snow storming outside. Kitchen had everything you'd want. Snow was plowed early in the morning. Stayed with wife and 2 teenage daughters and 2 dogs. Would come back. Thank you!
Guest favourite
Chalet in Winhall
4.89 out of 5 average rating, 81 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.
Guest favourite
Chalet in Dover
4.9 out of 5 average rating, 41 reviews

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

TedRating, 5 stars3 weeks ago
Nice amenities. Bit smaller than expected from the photos but everything is as advertised.
Top Guest favourite
Chalet in Wilmington
5 out of 5 average rating, 94 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

AmyRating, 5 stars2 months 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!
Top Guest favourite
Chalet in Winhall
5 out of 5 average rating, 50 reviews

Summer Fun in Winhall! Family Game Room & Deck!

BryanRating, 5 stars1 month ago
This was an enjoyable stay. Slept 6 comfortably. We also had such a great time in the game room playing pool, watching tv, and utilizing the arcade games. Totally recommend!
Guest favourite
Chalet in Winhall
4.93 out of 5 average rating, 40 reviews

Stratton Chalet w/ Golf Simulator and Hot Tub

RyanRating, 5 stars2 weeks ago
Great place to stay if you are looking to travel with a mid-sized group. There was always something to do at the house and it was reachable from downtown Manchester and the Stratton Village.
Superhost
Chalet in Wilmington
5 out of 5 average rating, 3 reviews

Exclusive house on the Lake. Min from town and Ski

JoshRating, 5 stars5 months ago
We had a fantastic stay at this beautiful property! The host was incredibly communicative, accommodating, and friendly, making every step smooth and stress-free. We were amazed at how immaculate and spacious it was. The attention to detail was exceptional—everything was sparkling clean, well-organized, and styled to feel both cozy and luxurious. One of the highlights of our trip was waking up to the stunning views right outside the windows. The private location gave us a sense of peaceful seclusion, yet it was surprisingly easy to reach the nearby mountain, as well as shops and restaurants, which made our days flexible and convenient. Whether we were enjoying the breathtaking scenery or exploring local attractions, we never felt rushed or cramped. It was the perfect getaway for my sons and me, and we can’t wait to come back. I highly recommend this wonderful place to anyone looking for a relaxing yet adventure-filled stay!
Top Guest favourite
Chalet in Winhall
5 out of 5 average rating, 27 reviews

Luxurious Fireside Lodge w/Stratton View

ChrisRating, 5 stars3 weeks ago
Had a group of 13 friends together for the long weekend and it was fantastic. The check-in and out process was smooth, the house was well organized and equipped with things you need for the kitchen, and plenty of firewood for the indoor and outdoor fireplaces. House was well done with a gigantic main room for everyone to hang out in, either on the comfortable couch and easy chairs, rocking chairs, dining table, or around the stunning kitchen island. Nice view of the mountains. Vermont surrounds are beautiful! Would come again!

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