
Chalet holiday rentals in Winhall
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Winhall
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 Winhall chalet rentals
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

5BR Chalet in Historic Town bet Killington & Okemo
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

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!

Mountain Chalet + HOT TUB
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

Hilltop Chalet on 20 rolling acres
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

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!
Luxury chalet rentals

Mountain Chalet: Private Brook - Hot Tub - Firepit
Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.

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!

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.

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

New! Custom Chalet minutes from Mt Snow w/ Hottub
The house was fantastic. Great condition, cool layout! There was a ton of snow, and the property was well plowed, shoveled and sanded!

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow
We really enjoyed our stay! The house is beautiful and perfect location for skiing at Mt snow or Stratton. Indoor hot tub was a huge hit & spacious living spaces were great for spending quality time together!

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!

Spacious Vermont Chalet for Group Getaways
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.
Quick stats about chalet rentals in Winhall
Total rentals
40 properties
Nightly prices starting at
$172 AUD 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
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Plainview Holiday rentals
- Cape Cod Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Condo rentals Winhall
- Kid-friendly rentals Winhall
- Rentals with a fire pit Winhall
- Rentals with outdoor seating Winhall
- Rentals with lake access Winhall
- Pet-friendly rentals Winhall
- Rentals with a hot tub Winhall
- Rentals with a washing machine and dryer Winhall
- Rentals with a patio Winhall
- Rentals with a fireplace Winhall
- Fitness-friendly rentals Winhall
- Ski-in/ski-out rentals Winhall
- Townhouse rentals Winhall
- Rentals with a sauna Winhall
- Family-friendly rentals Winhall
- Apartment rentals Winhall
- Rentals with pools Winhall
- Cabin rentals Winhall
- House rentals Winhall
- Chalet 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
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Spa State Park
- 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
- Ekwanok Country Club
- Lake George Expedition Park
- Baker Hill Golf Club
- Bretwood Golf Course
- Hooper Golf Course
- Dorset Field Club
- Clarksburg State Park
- Peebles Island State Park
- Hildene, The Lincoln Family Home
- Pineridge Cross Country Ski Area