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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
4.86 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 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!
Guest favourite
Chalet in Dover
4.82 out of 5 average rating, 62 reviews

Mt. Snow Slow Lane Lodge

EmilyRating, 5 stars8 months ago
The house and the surroundings were beautiful! There was lots to do and see, and it was an overall great time!
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 stars2 months 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.
Guest favourite
Chalet in Winhall
4.93 out of 5 average rating, 46 reviews

Le Chalet : beautiful renovated home - Stratton

CathyRating, 5 stars3 months ago
The best way I can explain our stay was that it felt like home. We are a family of six adults and four children ages 2-8. We spent most of our time on the top floor living area. The large kitchen island fit all ten of us, and we were able to eat all our meals together. The house was very clean and had everything we needed. There was a lot of snow on the property, so we were able to do some tubing in the backyard. It was a quick trip to Stratton Mountain each morning. Max was a great host. He ensured that the driveway was well plowed after a recent storm. He was quick to respond to any question, but we really did not need much help as everything was in order.
Superhost
Chalet in Dover
4.83 out of 5 average rating, 6 reviews

Relaxing Retreat in the Heart of Dover

DiedraRating, 5 stars1 week ago
Home is very spacious and clean. Great communication from host and very accommodating. Only problem we encountered was a guy would pull in front of the home at 1-2am and play loud music and sit there for hours. Came back the next day and did the exact same thing. Other than that, the place is perfect and as described. We would definitely stay again if in the area. It’s worth every penny and John is an educator so he gets mad props for his service to the community. Wish you the best and thanks for the great stay.
Superhost
Chalet in Dover
4.81 out of 5 average rating, 58 reviews

Spacious Vermont Chalet for Group Getaways

AnnaRating, 5 stars3 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.
Guest favourite
Chalet in Wardsboro
5 out of 5 average rating, 13 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

AlexisRating, 5 stars3 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 stars4 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!
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!

Destinations to explore