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Chalet vacation rentals in Bennington County

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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 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 favorite
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 favorite
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 favorite
Chalet in West Dover
4.98 out of 5 average rating, 51 reviews

Charming Chalet w. Hot Tub - 1 Mile to Mt. Snow

LaurenRating, 5 stars1 month ago
A beautiful spot perched amongst the trees and snowy woods. Cosy couches and fireplaces, a magical hot tub and generous touches, like extra wood, coffee and shampoo. I took my boys skiing nearby and we all loved every minute. Wouldn't hesitate to stay again
Guest favorite
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 favorite
Chalet in Wardsboro
5 out of 5 average rating, 57 reviews

Brook Haven Retreat - Minutes to Mt Snow&Stratton

CatherineRating, 5 stars2 weeks ago
We really enjoyed our stay here. It was super clean. We felt right at home. It was decorated beautifully and we found it very easy to relax. Our son LOVES the arcade game and referred to it as “the race car house”. It was really nice drinking coffee on the “treehouse deck” in the morning. And so relaxing hearing the water flowing in the brook at night.
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 favorite
Chalet in Winhall
4.96 out of 5 average rating, 95 reviews

Minutes to Stratton! Large, private home w. sauna

AliciaRating, 5 stars3 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 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 favorite
Chalet in Wardsboro
5 out of 5 average rating, 12 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

ChanaRating, 5 stars3 weeks ago
This house was perfect for our weekend family trip! The space was beautifully designed, thoughtfully laid out, and on the most wonderful peaceful and quiet road. It was a true Vermont mountains experience. The host was extremely responsive and helpful. We all loved it. Would recommend to anyone and definitely stay again.
Guest favorite
Chalet in Winhall
4.93 out of 5 average rating, 40 reviews

Stratton Chalet w/ Golf Simulator and Hot Tub

RyanRating, 5 stars4 days 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.

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