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Search results; Over 1,000 homes

Flat in Wintergreen Resort
1BR 2BA Cozy Retreat Steps from Wintergreen Resort
1 bedroom, 3 beds, 2 bathrooms
9–14 Aug
New place to stay
Superhost
Flat in Wintergreen Resort
Ski-In/Ski-Out + Blue Ridge Views | Wintergreen
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
14–19 Aug
4.92 out of 5 average rating, 213 reviews
Top guest favourite
Home in Wintergreen Resort
Close to hiking! | King Beds | Fireplace | Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 176 reviews
Guest favourite
Townhouse in Wintergreen Resort
Wintergreen home, ideal location, dogs welcome!
2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 214 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 177 reviews
Guest favourite
Flat in Wintergreen Resort
Wintergreen Escape | King Bed + Porch Views
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 124 reviews
Top guest favourite
Farm stay in Afton
Afton, Mountain View Mini Farm
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 345 reviews
Guest favourite
Flat in Wintergreen Resort
Wintergreen Getaway II
1 bedroom, 1 sofa bed, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Townhouse in Wintergreen Resort
Beary Lazy - 4 beds and 2 sleeping sofas!
2 bedrooms, 4 beds, 2.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Room in Roseland
Private Entrance Mountain Lodge Room/Nelson Rt151
2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 68 reviews
Top guest favourite
Cabin in Vesuvius
The Sanctuary
2 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
4.99 out of 5 average rating, 374 reviews
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Sleeps 12 • Breweries
4 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Wintergreen Resort
Cozy Condo on the mountain at Wintergreen!
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
4.87 out of 5 average rating, 135 reviews
Apartment in Wintergreen Resort
Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
4.84 out of 5 average rating, 171 reviews
Top guest favourite
Home in Wintergreen Resort
Luxury home Game room Sauna, Hot Tub, Pets Welcome
4 bedrooms, 10 beds, 3.5 bathrooms
7–12 Aug
4.97 out of 5 average rating, 35 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
4.94 out of 5 average rating, 192 reviews