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
Chalet in Plymouth
4.75 out of 5 average rating, 200 reviews5BR Chalet in Historic Town bet Killington & Okemo
Chalet in Mount Holly
4.97 out of 5 average rating, 147 reviewsCharming Summit View Chalet near Okemo and Lakes
Chalet in Stockbridge
4.86 out of 5 average rating, 76 reviewsPrivate House - Hot Tub, Steam Room, Fire pit
Chalet in Plymouth
4.96 out of 5 average rating, 68 reviewsOZ- 6BR Ski Chalet Between Killington & Okemo
Chalet in Ludlow
4.78 out of 5 average rating, 65 reviewsMountain Chalet with a HOT TUB
Chalet in Killington
4.86 out of 5 average rating, 70 reviewsWest Park Chalet at Killington: Great For Groups!
Chalet in Ludlow
4.68 out of 5 average rating, 141 reviews6-BR Ski Chalet w/Hot Tub near Okemo & Killington
Chalet in Killington
5 out of 5 average rating, 22 reviewsKillington Ski Chalet on Great Eastern Trail
Luxury chalet rentals
Chalet in Bridgewater
4.95 out of 5 average rating, 41 reviewsCozy VT Getaway w/ Hot Tub - 10 min to Killington
Chalet in Shrewsbury
4.94 out of 5 average rating, 36 reviewsPrivate Mtn Escape 37acres | 20min to Skiing
Chalet in Mount Holly
4.92 out of 5 average rating, 64 reviewsOkemo Hot Tub Fireplace Billiard
Chalet in Ludlow
4.87 out of 5 average rating, 77 reviewsOkemo Mountain-Newly Renovated w AC, hottub, WiFi
Chalet in Stockbridge
4.95 out of 5 average rating, 42 reviewsBENT TREE Vermont, Mtn Chalet 25 min to Killington
Chalet in Killington
5 out of 5 average rating, 53 reviewsBearHaus- HUGE Hot Tub, FirePit
Chalet in Killington
5 out of 5 average rating, 12 reviewsPRIME location w/HOT TUB! Gut Renovated 6 BR Home!
Chalet in Killington
5 out of 5 average rating, 5 reviews5 min Ski| 1 min Nightlife| Hot Tub| Arcade| Fires
Destinations to explore
- Chalet rentals United States
- Chalet rentals Vermont
- Chalet rentals Vermont
- Chalet rentals New York
- Chalet rentals New Hampshire
- Farmstay rentals Windsor County
- Cabin rentals Windsor County
- Rentals with a fire pit Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with lake access Windsor County
- Rentals with breakfast Windsor County
- Fitness-friendly rentals Windsor County
- Villa rentals Windsor County
- Monthly Rentals Windsor County
- Pet-friendly rentals Windsor County
- Apartment rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Waterfront rentals Windsor County
- Townhouse rentals Windsor County
- Rentals with a sauna Windsor County
- Beachfront rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Cottage rentals Windsor County
- Rentals with pools Windsor County
- Tiny house rentals Windsor County
- Rentals with an EV charger Windsor County
- Family-friendly rentals Windsor County
- Rentals with a kayak Windsor County
- Rentals with beach access Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Condo rentals Windsor County
- Rentals with a hot tub Windsor County
- Bed and breakfasts Windsor County
- Kid-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with a patio Windsor 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
- Things to do United States
- Sports activities United States
- Nature and outdoors United States
- Entertainment United States
- Art and culture United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Things to do Vermont
- Food and drink Vermont
- Things to do Windsor County
- Food and drink Windsor County