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Chalet holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Windsor County
Family-friendly chalet rentals
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Chalet in Stockbridge
4.86 out of 5 average rating, 76 reviewsPrivate House - Hot Tub, Steam Room, Fireplace
![](https://a0.muscache.com/im/pictures/9a0a636f-8fed-47a9-94d4-1981564fb30c.jpg?im_w=720)
Chalet in Ludlow
4.76 out of 5 average rating, 119 reviewsCharming Lakefront House
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Chalet in Plymouth
4.73 out of 5 average rating, 190 reviews5BR Chalet in Historic Town bet Killington & Okemo
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Chalet in Mount Holly
4.92 out of 5 average rating, 51 reviews3 bedroom mountain getaway
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Chalet in Ludlow
4.78 out of 5 average rating, 65 reviewsMountain Chalet with a HOT TUB
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Chalet in Mount Holly
4.97 out of 5 average rating, 143 reviewsCharming Summit View Chalet near Okemo and Lakes
![](https://a0.muscache.com/im/pictures/miso/Hosting-38219/original/c0e7dd50-43e4-4bac-814f-24053a040ec6.jpeg?im_w=720)
Chalet in Ludlow
4.68 out of 5 average rating, 141 reviews6-BR Ski Chalet w/Hot Tub near Okemo & Killington
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Chalet in Plymouth
5 out of 5 average rating, 41 reviewsFour Season Mountain Chalet w/ sauna & fireplace
Luxury chalet rentals
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Chalet in Killington
4.98 out of 5 average rating, 41 reviewsThe Overlook | Hot Tub | Fire Pit | Views | Games
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Chalet in Killington
5 out of 5 average rating, 44 reviewsBearHaus- Central AC, HUGE Hot Tub, FirePit
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Chalet in Ludlow
5 out of 5 average rating, 25 reviewsCozy Ski Retreat Ludlow Village 3 Minutes to Okemo
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Chalet in Ludlow
4.89 out of 5 average rating, 19 reviewsLuxury 8BR Ski In/Out Okemo Chalet Sleeps 22
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Chalet in Londonderry
5 out of 5 average rating, 23 reviewsLovely Home with a Sauna. Minutes to 3 mountains!
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Chalet in Stockbridge
4.95 out of 5 average rating, 41 reviewsBENT TREE Vermont, Mtn Chalet 20 min to Killington
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Chalet in Plymouth
4.96 out of 5 average rating, 68 reviewsOZ- 6BR Ski Chalet Between Killington & Okemo
![](https://a0.muscache.com/im/pictures/6b7e6141-9efe-4e15-b991-586e23feeadb.jpg?im_w=720)
Chalet in Killington
4.96 out of 5 average rating, 26 reviewsIdeal for families and groups, large yard to play
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