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Chalet vacation 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

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 Manchester Center
4.84 out of 5 average rating, 109 reviews

Private forest retreat near town, AT/LT trails

ConnorRating, 5 stars2 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.
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 stars2 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, 445 reviews

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

OscarRating, 5 stars1 week 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 stars4 months ago
Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.

Luxury chalet rentals

Guest favorite
Chalet in Winhall
4.92 out of 5 average rating, 26 reviews

Luxury, King Beds, 4 Pvt Baths , 3 min to golf

ChrisRating, 5 stars1 month ago
This place is a true gem at Stratton Mnt. The house is very close to the resort a 1min drive or you can also walk. House is super clean bathrooms are all amazing decor is nice. Also if you’re not into Stratton Mtn lots of things to do with 20 mins from this place including Manchester. Highly recommend host are so nice and great communication.
Guest favorite
Chalet in Winhall
4.92 out of 5 average rating, 36 reviews

1970's Classic Ski Chalet - Stratton Mountain

CaraRating, 5 stars2 months ago
The 70’s chalet is its name sake! Cozy and close to the mountain. The fireplace and downstairs room make it a great after ski relaxation spot! And it’s 5 minutes to Stratton Mountain!
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 Dover
4.95 out of 5 average rating, 19 reviews

Luxury Retreat in Mount Snow, VT

ChristinaRating, 5 stars3 months ago
We had a fantastic time at Philippe’s home in Dover. The house was charming, impeccably clean, and offered amazing views. It was thoughtfully stocked with everything we needed, and the beds were incredibly comfortable. During our stay, we experienced significant snowfall, but the streets and driveway were promptly plowed, making everything easily accessible. The location was perfect—just minutes from Mount Snow. We had an unforgettable trip and can’t wait to return soon!
Guest favorite
Chalet in Winhall
4.96 out of 5 average rating, 95 reviews

Minutes to Stratton! Large, private home w. sauna

AliciaRating, 5 stars2 months ago
We had a wonderful stay at Zach and Tasha’s place. Perfect house for our 2 families with kids. Close to Stratton Mountain. Very clean house and well equipped. The sauna was our favorite part! Will come back for sure!
Top guest favorite
Chalet in Manchester
5 out of 5 average rating, 49 reviews

Luxury Village Chalet w/ GuestHouse -Pet Friendly

GailRating, 5 stars2 months ago
We had an excellent time! This home was the perfect spot for our family ski trip. It's so close to town and to multiple mountains (Bromley/Stratton/Magic). The house was beautiful and clean. The open layout on the first floor worked perfectly for our mix of kids and adults. Maybe most importantly, the beds were comfortable with high quality linens - really makes a difference! Beautiful home and highly recommend!
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 stars3 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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