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Chalet holiday rentals in Winhall

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Popular amenities for chalet rentals in Winhall

Family-friendly chalet rentals

Superhost
Chalet in Peru
4.88 out of 5 average rating, 64 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
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!
Guest favourite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars8 months ago
My wife and I thoroughly enjoyed our stay at John's Chalet. The house was exactly as described beautiful inside and out. We loved seeing all the wildlife around the home every day. The home is very private and close to many outdoor activities especially hiking. We would certainly consider this home again on our next trip to Vermont. Sincerely Paul & Rebecca
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 453 reviews

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

JasonRating, 5 stars2 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.
Guest favourite
Chalet in Ludlow
4.95 out of 5 average rating, 128 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars3 weeks ago
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.
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
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.

Luxury chalet rentals

Guest favourite
Chalet in Dover
5 out of 5 average rating, 48 reviews

Authentic Vermont Chalet: Year Round Vacation Home

ChristinaRating, 5 stars3 months ago
Beautiful spot with a cozy yet spacious house. Instructions were very clear on how to get in and the different features of the house. Perfect for a relaxing get-away with friends!
Top guest favourite
Chalet in Wilmington
5 out of 5 average rating, 62 reviews

Beautiful Home on 22 Acres w/Ponds & Central A/C

Christopher WRating, 5 stars1 month ago
Beautiful place. The house, the land. My family of 5 and our dog loved it. The kids loved the ponds and the games room. Vanessa was a great host and helped make it a great experience from start to finish. Cheers!
Top guest favourite
Chalet in Dover
5 out of 5 average rating, 35 reviews

Charming Mountain Chalet w/ Spa near Mt Snow

Caitlin Rating, 5 stars2 months ago
Lovely stay in a cozy, comfortable house only 15 minutes from Mount Snow. We enjoyed post ski-day nights by the fire, with plenty of comfortable seating and board games galore. The yard was great for our dogs and features like the koi pond and hot tub were easy to enjoy in a peaceful and private environment. We’ll be back!
Top guest favourite
Chalet in Sunderland
4.99 out of 5 average rating, 81 reviews

Serene & Stylish Chalet w/ HOT TUB near Manchester

MingRating, 5 starstoday
Wonderful chalet close to all of the best of Southern Vermont. A nice blend of modern comfort and rustic surroundings. Beautiful private yard for roasting marshmallows and hot tubbing. Garrett was very responsive whenever we had a question or needed assistance. One of the most responsive hosts we’ve had over the past 10 years of using AirBNB. Super host indeed
Guest favourite
Chalet in Wardsboro
4.89 out of 5 average rating, 44 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

ZackRating, 5 stars1 month ago
absolutely gorgeous place with a beautiful veiw as stated i wpuld 10/10 stay again highly recommended property for familes or friends always responded well too
Guest favourite
Chalet in Dover
4.9 out of 5 average rating, 40 reviews

Hot Tub-TheaterRm-Game Room-FirePit-1mi To Mt Snow

TedRating, 5 stars2 weeks ago
Nice amenities. Bit smaller than expected from the photos but everything is as advertised.
Guest favourite
Chalet in Winhall
4.93 out of 5 average rating, 40 reviews

Stratton Chalet w/ Golf Simulator and Hot Tub

RyanRating, 5 stars1 week 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.
Top guest favourite
Chalet in Winhall
5 out of 5 average rating, 27 reviews

Luxurious Fireside Lodge w/Stratton View

ChrisRating, 5 stars2 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!

Quick stats about chalet rentals in Winhall

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹9,468 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall
  6. Chalet rentals