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

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!

Luxury of large space by ski slopes, deck HOT TUB
Our stay at Hideaway was relaxing and exactly how we expected it. The cabin is within a short driving distance from the ski areas and grocery stores, and very comfortable for a family with two children. The host was easy to reach and responded quickly to communication. Overall, a wonderful vacation.

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

Charming Lakefront House
This home was just what we were looking for. It is charming and spacious, rustic in all of the right ways, with a gorgeous view of the lake, and so close to Okemo. The master bedroom was huge, and we really enjoyed the large communal space with the wood-burning stove. Some of us were cooking while others were playing games, while others were relaxing by the fire, so that we could all easily enjoy each other‘s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.

Killington Ski Chalet on Great Eastern Trail
This house is amazing! Our family Killington trip was enhanced by staying at this beautiful chalet. The pictures online do not do this property justice as it is much more beautiful in person! The kitchen is very well stocked with everything you need, the house was clean and immaculate with enough linens for everyone. Virginia was responsive to any questions and very welcoming. We had a snowstorm, and the plow came promptly to plow the driveway. There is an echo from the loft in the main floor, and it is much quieter on the lower level. There was ample wood for the fireplace. We would love to come again next year!

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

3 bedroom mountain getaway
My friends and I had a great stay at Daniel’s place! It was very clean with plenty of space to accommodate all of us. We were skiing at Okemo, which was a quick 15 minute drive. Would definitely recommend staying here!

Viewmont Chalet - Beautiful post and beam house wi
Great cabin - very spacious and close to the hill. Amenities (pool table, hot tub) were also nice.
Luxury chalet rentals

Chalet Schlosser
Chalet Schlosser was perfect for our short vacation week excursion. Plenty of beds for a couple families, super cozy, and everything worked as advertised, including the fireplace which kept us warm and helped dry our gear. Really convenient to Killington lodges, easy drive to town, driveway was plowed and cleaned during a storm while we were there without needing to ask about it. The "chalet" was the cherry on top of a great weekend.

Classic Ski Chalet+ wood fireplace+chef’s kitchen
We had a great weekend here. It was comfortable with the 8 of us in this house. It was cozy with the fireplace, we utilized the grill and the ping pong table. The location was great for our skiing weekend! Very close to Killington and Pico.

Secluded 4BR cabin w/ HOT TUB- Walk to Access Rd!
Place was great, couple of minute drive to the mountain, nightlife was right around the corner and the accommodation had a ton of space.

Overlook | AC | Hot Tub | Fire Pit | Views | Games
Beautiful home right down the street from Killington. The views are what makes this place special... The house is equipped with more than what's needed. There are so many towels and throw blankets. If this house is available, you won't regret it!

BENT TREE Vermont, Mtn Chalet 25 min to Killington
Beautiful location and very easy access to Killington Ski Resort! We had >1 foot of snow and the steep driveway was plowed well before departure. Very clear communication and instructions made for a very relaxing time. Thank you for sharing your home!

BearHaus- Central AC, HUGE Hot Tub, FirePit
Very family friendly ski rental. Thank you!

Cozy Chalet near Okemo Jacuzzi/Sauna
My family and I had a great week at Gabriella's place in Mt. Holly. It is a 5 min drive from Jackson Gore Base at Okemo, which made for very easy skiing (and parking!). Gabriella was responsive and friendly when we checked in. We happened to be there during a snowstorm and the drive was plowed by midmorning the next day. It was also very cold, and despite the somewhat quirky heating, we were able to stay warm while at the house. My husband and daughter enjoyed the foosball in the basement (not heated, but does have plug in heater). Hot tub was great. Only thing guests might want to note is that there are limited pots and cooking supplies so it was challenging to make meals. Also, the dishes provided are melamine/not microwave safe so we bought paper plates for when we wanted to reheat food. The home is, however, well stocked with glasses, coffee cups, baking dishes, and pans. Beds were comfy. Heated mats on front steps were very helpful. All in all, a great stay and would rent again!

5 min Ski| 1 min Nightlife| Hot Tub| Arcade| Fires
Awesome place and location! Andrew was very responsive and the house was very clean. Just a quick shuttle ride to the downtown area and only minutes from the mountain. I will definitely be staying again
Destinations to explore
- Waterfront rentals Windsor County
- Cottage rentals Windsor County
- Farmstay rentals Windsor County
- Villa rentals Windsor County
- Rentals with a hot tub Windsor County
- Townhouse rentals Windsor County
- Rentals with pools Windsor County
- Cabin rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Condo rentals Windsor County
- Rentals with an EV charger Windsor County
- Ski-in/ski-out rentals Windsor County
- Tiny house rentals Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Kid-friendly rentals Windsor County
- Family-friendly rentals Windsor County
- Rentals with a sauna Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
- Pet-friendly rentals Windsor County
- Rentals with a patio Windsor County
- Apartment rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with breakfast Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with a fire pit Windsor County
- Rentals with beach access Windsor County
- Rentals with lake access Windsor County
- Beachfront rentals Windsor County
- Rentals with a kayak Windsor 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
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Monadnock State Park
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Hooper Golf Course
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Fort Ticonderoga
- Northeast Slopes Ski Tow
- Dartmouth Skiway
- Mount Sunapee Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Killington Adventure Center
- Santa's Land USA
- Brattleboro Ski Hill
- Fox Run Golf Club
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Nature and outdoors Vermont
- Food and drink Vermont
- Things to do United States
- Sightseeing United States
- Art and culture United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Tours United States
- Food and drink United States