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Chalet holiday rentals in Bennington County

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Bennington County

Family-friendly chalet rentals

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

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

KarenRating, 5 stars1 week ago
We had a great time at the cabin. Although there are other cabins on the property, it felt private. The space was very roomy and comfy. We loved the record player, and I looked at every record and played many of them! We took our own sheets and towels, but all that was at the cabin when we got there, so we didn't need them. It was nice to find empty kitchen cupboards for our own stuff, so we didn't have to rearrange everything :) And we've had a run of vacation rentals with foot high grass lately, so it was nice to see Jason mowing the lawn on our third day there. All in all, it was a great stay
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!
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
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.
Top guest favourite
Chalet in Sunderland
4.99 out of 5 average rating, 80 reviews

Serene & Stylish Chalet + HOT TUB near Manchester

TimRating, 5 stars1 week ago
Garrett was responsive and allowed us to check in early as his Chalet was cleaned and ready for us early. Great host!! Welcome basket with hoodies and a host note to our group. Great!!
Superhost
Chalet in Dover
4.8 out of 5 average rating, 5 reviews

Relaxing Retreat in the Heart of Dover

KaitlynRating, 5 stars2 weeks ago
This Airbnb was the perfect fit for my group and I while we visited Vermont. The house was located in a great area where it was close to everything you would need or want to visit. The house was also very spacious for my group and very clean.
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.
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.
Top guest favourite
Chalet in Wilmington
5 out of 5 average rating, 94 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

AmyRating, 5 stars1 month 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!
Guest favourite
Chalet in Wardsboro
5 out of 5 average rating, 13 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

AlexisRating, 5 stars2 weeks ago
We had the most amazing weekend getaway with a group of 12 close friends! The house was cozy, beautifully decorated, and felt like the perfect home away from home. Despite it being a rainy Memorial Day weekend, we had the best time just enjoying the space together. The backyard was stunning, a great place for walking out in the morning with your cup of coffee. The kitchen was a total highlight: spacious, well-stocked with everything we needed, and perfect for cooking and feasting with a group. This stay gave us such great memories, and we’re so grateful to the hosts for creating such a warm and welcoming space. Would absolutely recommend and hope to return someday!
Top guest favourite
Chalet in Winhall
5 out of 5 average rating, 50 reviews

Summer Fun in Winhall! Family Game Room & Deck!

BryanRating, 5 stars3 weeks 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!

Destinations to explore