
Chalet holiday rentals in Bennington County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Bennington County
Guests agree: these chalets are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Bennington County
Family-friendly chalet rentals

Getaway in Green Mountains
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

Private forest retreat near town, AT/LT trails
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.

Rustic Sunny Vermont Home near Mount Snow
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!

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

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic

Cozy House - Mount Snow, VT
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!

Vermont House, near Bromley Park and Hapgood Beach
Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.

Bromley Aframe - King Master Bed, Wood Fireplace
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

A quintessential Vermont getaway
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.

Serene & Stylish Chalet + HOT TUB near Manchester
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!!

Relaxing Retreat in the Heart of Dover
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.

Spacious Chalet W/ Endless Entertainment THE BARN
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.

Hot Tub-TheaterRm-Game Room-FirePit-1mi To Mt Snow
Nice amenities. Bit smaller than expected from the photos but everything is as advertised.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
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!

Modern Lux Cabin w/ Mtn Views | Fire Pit
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!

Summer Fun in Winhall! Family Game Room & Deck!
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
- Rentals with a hot tub Bennington County
- Rentals with a kayak Bennington County
- Bed and breakfasts Bennington County
- Cabin rentals Bennington County
- Rentals with a sauna Bennington County
- Rentals with an accessible-height toilet Bennington County
- House rentals Bennington County
- Ski-in/ski-out rentals Bennington County
- Rentals with breakfast Bennington County
- Hotel rentals Bennington County
- Apartment rentals Bennington County
- Flat rentals Bennington County
- Pet-friendly rentals Bennington County
- Rentals with a fireplace Bennington County
- Rentals with outdoor seating Bennington County
- Rentals with a washing machine and dryer Bennington County
- Family-friendly rentals Bennington County
- Private suite rentals Bennington County
- Farm stay rentals Bennington County
- Rentals with a firepit Bennington County
- Rentals with a patio Bennington County
- Rentals with pools Bennington County
- Fitness-friendly rentals Bennington County
- Townhouse rentals Bennington County
- Rentals with lake access Bennington County
- Family-friendly rentals Bennington County
- Chalet rentals Vermont
- Chalet rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Albany Center Gallery
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Lake George Expedition Park
- Dorset Field Club
- Canterbury Farm
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Ekwanok Country Club
- Brattleboro Ski Hill