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Search results; Over 1,000 homes

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Wintergreen Resort
Ty's Retreat: Cozy 2-bedroom condo with fireplace
2 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
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4.97 out of 5 average rating, 71 reviews
Guest favourite
Home in Wintergreen Resort
Wood-burning fireplace on the golf course
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Guest favourite
Apartment in Wintergreen Resort
Ski-in/ski-out with Blue Ridge views
4.95 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
Guest favourite
Chalet in Wintergreen Resort
Walkable to slopes with a fireplace
4.94 out of 5 average rating, 187 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Nellysford
Mountain Bauhaus with a fire pit
4.9 out of 5 average rating, 128 reviews, 4 bedrooms, 2.5 bathrooms
19–24 Jul
Guest favourite
Flat in Wintergreen Resort
Wintergreen Getaway
4.86 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4.95 out of 5 average rating, 239 reviews, 4 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Home in Afton
Octagonal house with 180-degree mountain views
4.99 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Wintergreen Resort
Mountain retreat with fireplace and fire pit
4.9 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
4.92 out of 5 average rating, 128 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
15–20 Jul
Top guest favourite
Flat in Wintergreen Resort
Ridge-top penthouse with sauna and fireplace
4.98 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 4 bathrooms
15–20 Jul
Top guest favourite
Home in Wintergreen Resort
Cozy Wintergreen Townhome
4.96 out of 5 average rating, 27 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
18–23 Jul
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
4.9 out of 5 average rating, 83 reviews, 3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Chalet in Wintergreen Resort
Ski-in/ski-out with mountain views
5.0 out of 5 average rating, 89 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
15–20 Jul
Top guest favourite
Bungalow in Afton
Remodeled, steps from Veritas Vineyard
4.99 out of 5 average rating, 247 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
4.9 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Superhost
Apartment in Wintergreen Resort
Wooded patio views near hikes and breweries
4.92 out of 5 average rating, 207 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Aug
Guest favourite
Cabin in Wintergreen Resort
Double-height great room with a hot tub
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Jul
Apartment in Wintergreen Resort
Ski-in/ski-out with two fireplaces
4.84 out of 5 average rating, 169 reviews, 3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul