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
4.74 out of 5 average rating, 196 reviews5BR Chalet in Historic Town bet Killington & Okemo
Chalet in Mount Holly
4.97 out of 5 average rating, 146 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 Ludlow
4.78 out of 5 average rating, 65 reviewsMountain Chalet with a HOT TUB
Chalet in Rochester
5 out of 5 average rating, 43 reviewsMountain Bliss: Spacious Retreat Near Killington
Chalet in Plymouth
4.96 out of 5 average rating, 68 reviewsOZ- 6BR Ski Chalet Between Killington & Okemo
Chalet in Killington
4.86 out of 5 average rating, 69 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
Luxury chalet rentals
Chalet in Mendon
5 out of 5 average rating, 15 reviewsUnique Luxury- Secret Door-Minutes to Ski Resorts
Chalet in Ludlow
4.91 out of 5 average rating, 22 reviewsLuxury 8BR Ski In/Out Okemo Chalet Sleeps 22
Chalet in Ludlow
4.87 out of 5 average rating, 75 reviewsOkemo Mountain-Newly Renovated w AC, hottub, WiFi
Chalet in Killington
4.98 out of 5 average rating, 48 reviewsThe Overlook | Hot Tub | Fire Pit | Views | Games
Chalet in Stockbridge
4.95 out of 5 average rating, 42 reviewsBENT TREE Vermont, Foliage Getaway over VT Rte 100
Chalet in Woodstock
4.95 out of 5 average rating, 99 reviewsStunning Riverfront Inn - Close to Ski w/ Hot Tub
Chalet in Killington
5 out of 5 average rating, 51 reviewsBearHaus- HUGE Hot Tub, FirePit
Chalet in Killington
5 out of 5 average rating, 11 reviewsPRIME location w/HOT TUB! Gut Renovated 6 BR Home!
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