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 Shrewsbury
4.94 out of 5 average rating, 36 reviewsPrivate Mtn Escape 37acres | 20min to Skiing
Chalet in Killington
4.86 out of 5 average rating, 58 reviewsRiverfront 4BR cabin w/ HOT TUB- Recently Updated!
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 Mount Holly
4.89 out of 5 average rating, 27 reviewsCozy Chalet near Okemo Jacuzzi/ SAUNA
Chalet in Killington
5 out of 5 average rating, 5 reviewsViewmont Chalet - Beautiful post and beam house wi
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