Chalet vacation rentals in Windsor County
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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 Stockbridge
4.86 out of 5 average rating, 76 reviewsPrivate House - Hot Tub, Steam Room, Fireplace
Chalet in Ludlow
4.76 out of 5 average rating, 118 reviewsCharming Lakefront House
Chalet in Mount Holly
4.92 out of 5 average rating, 51 reviews3 bedroom mountain getaway
Chalet in Killington
4.85 out of 5 average rating, 61 reviewsBigelow Chalet at Killington
Chalet in Plymouth
4.96 out of 5 average rating, 67 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 Ludlow
4.96 out of 5 average rating, 112 reviewsOkemo Ski Chalet with Hot Tub
Chalet in Mount Holly
4.96 out of 5 average rating, 142 reviewsCharming Summit View Chalet near Okemo and Lakes
Luxury chalet rentals
Chalet in Killington
5.0 out of 5 average rating, 39 reviewsThe Overlook | Hot Tub | Game Room | 5min to MTN
Chalet in Stockbridge
4.96 out of 5 average rating, 24 reviewsOff grid Eco-chalet; private mtn 360 view
Chalet in Killington
5.0 out of 5 average rating, 42 reviewsBearHaus- Central AC, HUGE Hot Tub, FirePit
Chalet in Ludlow
4.86 out of 5 average rating, 70 reviewsOkemo Mountain-Newly Renovated w AC, hottub, WiFi
Chalet in Killington
5.0 out of 5 average rating, 8 reviewsPRIME location w/HOT TUB! Gut Renovated 6 BR Home!
Chalet in Stockbridge
4.95 out of 5 average rating, 41 reviewsBENT TREE Vermont, Mtn Chalet 20 min to Killington
Chalet in Killington
4.97 out of 5 average rating, 70 reviews5BR, 4BA -WALK Downtown-2min to MTN
Chalet in Killington
4.98 out of 5 average rating, 50 reviewsChateau Charmaine
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