Ski-in/Ski-out vacation rentals in Windsor County
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Windsor County
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windsor County ski-in/ski-out rentals
Ski-in/ski-out house rentals
Home in Ludlow
5 out of 5 average rating, 7 reviewsStay at our renovated Okemo chalet
Home in Killington
4.88 out of 5 average rating, 51 reviewsKillington Ski Condo: Your Winter Escape!
Home in Killington
4.94 out of 5 average rating, 48 reviewsSki On/Ski Off Condo Pico/Killington Mountain
Home in Ludlow
New place to staySki-In/Ski-Out Hike Okemo Mountain Condo
Home in Ludlow
5 out of 5 average rating, 3 reviewsOkemo Condo - Ski In/Out
Home in Ludlow
4.92 out of 5 average rating, 89 reviewsWalk to Okemo Ski Lift - Private Classic VT Ski Ch
Home in Killington
4.87 out of 5 average rating, 31 reviewsScenic 5 Bedroom Killington Mountain Vacation Home
Home in Ludlow
5 out of 5 average rating, 3 reviews2BR/2.5 Bath at Solitude Okemo
Family-friendly, ski-in/ski-out home rentals
Condo in Ludlow
4.95 out of 5 average rating, 110 reviewsSlopeside condo at the base of Okemo-steps to lift
Yurt in Orange County
4.8 out of 5 average rating, 70 reviews24' yurt-stay
Rental unit in Chester
4.89 out of 5 average rating, 491 reviewsBeautiful 2 Bedrooms in Mountains w/ full kitchen
Rental unit in Ludlow
4.91 out of 5 average rating, 141 reviewsGreat Downtown, walk to everything
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Townhouse in Ludlow
4.93 out of 5 average rating, 58 reviewsOkemo village townhouse. Private indoor hot tub.
Condo in Killington
4.93 out of 5 average rating, 82 reviews⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
Condo in Killington
4.86 out of 5 average rating, 112 reviewsMountain Retreat: 4 Bdrm/2 Bath, Ski In, Bus Out
Ski-in/ski-out cabin rentals
Cabin in Peru
4.79 out of 5 average rating, 82 reviewsThe Grateful Barn
Cabin in Sharon
4.93 out of 5 average rating, 27 reviews‘Owls Nest’ nature retreat In the trees
Cabin in Mendon
4.84 out of 5 average rating, 238 reviewsTHE CABIN....a Vermont log home
Cabin in Londonderry
4.75 out of 5 average rating, 379 reviewsBeautiful Art Studio with hot tub/sauna #1 Airbnb
Cabin in Rutland
New place to stayBlue Cozy Ski House
Cabin in Stockbridge
5 out of 5 average rating, 21 reviewsRustic charming camp cabin
Cabin in Bethel
4.95 out of 5 average rating, 65 reviewsThe Gourmet Cabin at Stitchdown Farm
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