
Chalet holiday rentals in Bennington County
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Top-rated chalet rentals in Bennington County
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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.

Beautiful chalet for any season
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!

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
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 :))))

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!

Valley Chalet minutes to Manchester, restaurants
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!

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

1970's Classic Ski Chalet - Stratton Mountain
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!

4+BR pet-friendly w/ hot tub & Stratton parking!
Great house, as described. Very responsive host before and during the stay with clear instructions. The couple of things that stood out: 1. Big house; easily sleeps 10, can get a couple more kids in if you want. 2. 15 minutes to Stratton with a parking permit provided which was key. 3. Indoor garage space was great, especially as it was snow storming outside. Kitchen had everything you'd want. Snow was plowed early in the morning. Stayed with wife and 2 teenage daughters and 2 dogs. Would come back. Thank you!

Luxury Retreat in Mount Snow, VT
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!

Brook Haven Retreat - Minutes to Mt Snow&Stratton
We had a great weekend at this Airbnb! The hosts were super helpful & responsive - even letting us check in hours early. The space was clean, the kitchen was stocked & there were plenty of games which came in handy during the rain. The stream is just behind the house and so nice to sit next to it. Very dog friendly as well. Would definitely recommend.

Minutes to Stratton! Large, private home w. sauna
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!

Luxury Village Chalet w/ GuestHouse -Pet Friendly
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!

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!

The Great Escape!
We had a wonderful stay at the Great Escape! Nicely decorated, cozy and very comfortable for our family ski weekend. Highly recommend. Brianne is a great host, friendly and quick to respond!
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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Lake George Expedition Park
- National Museum of Racing and Hall of Fame
- Huck Finn’s Playland, Albany
- Peebles Island State Park
- Northern Cross Vineyard