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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

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 stars3 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.
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!

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.
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.
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
Superhost
Chalet in Dover
4.81 out of 5 average rating, 58 reviews

Spacious Vermont Chalet for Group Getaways

AnnaRating, 5 stars4 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.
Superhost
Chalet in Dover
4.8 out of 5 average rating, 35 reviews

Beautiful Mt. Snow 3 Bed 2 Bath Chalet W/ Hot Tub

WilliamRating, 5 stars3 months ago
The place was exactly as advertised. Everything was clean and well organized. We were very conveniently located by Mount Snow, and there were plenty of local restaurants as dinner options.
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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