Chalet vacation rentals in Windham County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Windham 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 Windham County chalet rentals
Family-friendly chalet rentals
Chalet in Peru
4.88 out of 5 average rating, 57 reviewsBromley Aframe - King Master Bed, Wood Fireplace
Sep 6 – 13
Chalet in Wilmington
4.94 out of 5 average rating, 89 reviewsRustic Sunny Vermont Home near Mount Snow
Oct 11 – 18
Chalet in Wilmington
4.56 out of 5 average rating, 89 reviewsCozy House - Mount Snow, VT
Aug 5 – 12
Chalet in Londonderry
4.87 out of 5 average rating, 107 reviewsGorgeous Stratton view, great for families
Nov 15 – 22
Chalet in Peru
4.91 out of 5 average rating, 58 reviewsGetaway in Green Mountains
Aug 26 – Sep 2
Chalet in Jamaica
4.97 out of 5 average rating, 66 reviewsSpacious and Private Chalet close to Stratton
Nov 8 – 15
Chalet in Winhall
4.79 out of 5 average rating, 71 reviewsBeautiful chalet for any season
Jan 30 – Feb 6
Chalet in Dover
4.82 out of 5 average rating, 60 reviewsMt. Snow Slow Lane Lodge
Nov 27 – Dec 4
Luxury chalet rentals
Chalet in Dover
5.0 out of 5 average rating, 14 reviewsGreen Mt Chalet: Magical Summer Hideaway w/Hot Tub
Feb 24 – Mar 3
Chalet in Dover
4.97 out of 5 average rating, 69 reviewsModern Mountain Chalet: hot tub-firepit-brook
Mar 5 – 12
Chalet in Wilmington
5.0 out of 5 average rating, 39 reviewsBeautiful Home on 22 Acres w/Ponds Near Mt. Snow
Oct 30 – Nov 6
Chalet in Winhall
4.98 out of 5 average rating, 54 reviewsMountain view chalet with hot tub & fire pit!
Feb 26 – Mar 5
Chalet in Wardsboro
5.0 out of 5 average rating, 11 reviewsMaplebrook Chalet w/ Hot Tub, Fireplace & Firepit
Sep 22 – 29
Chalet in Winhall
5.0 out of 5 average rating, 37 reviewsStylish Getaway w/ Hot Tub close to Stratton
Sep 2 – 9
Chalet in Stratton
4.98 out of 5 average rating, 86 reviewsWooden Owl Lodge
Aug 16 – 23
Chalet in Winhall
4.97 out of 5 average rating, 87 reviewsLarge Private Stratton Home, Monthly discounts
Aug 29 – Sep 5
Destinations to explore
- Chalet rentals United States
- Chalet rentals Vermont
- Chalet rentals New York
- Chalet rentals New Hampshire
- Pet-friendly rentals Windham County
- Fitness-friendly rentals Windham County
- Cabin rentals Windham County
- Rentals with an EV charger Windham County
- Rentals with lake access Windham County
- Bed and breakfasts Windham County
- Waterfront rentals Windham County
- Townhouse rentals Windham County
- Rentals with outdoor seating Windham County
- Family-friendly rentals Windham County
- Tiny house rentals Windham County
- Condo rentals Windham County
- Rentals with a kayak Windham County
- Rentals with a hot tub Windham County
- Rentals with breakfast Windham County
- Monthly Rentals Windham County
- Rentals with a fireplace Windham County
- Beachfront rentals Windham County
- Rentals with pools Windham County
- Guesthouse rentals Windham County
- Rentals with a sauna Windham County
- Rentals with an accessible height toilet Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with beach access Windham County
- Private suite rentals Windham County
- Apartment rentals Windham County
- Rentals with a fire pit Windham County
- Rentals with a washer and dryer Windham County
- Farmstay rentals Windham County
- House rentals Windham County
- Kid-friendly rentals Windham County
- Rentals with a patio Windham County
- 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