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Search results; Over 1,000 homes

Descriptions are based on details hosts provide
Top guest favourite
Home in Wintergreen Resort
Cliffs Edge -A Contemporary Mountain Home
3 bedrooms, 4 beds, 3 shared bathrooms
20–25 Jul
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4.97 out of 5 average rating, 125 reviews
Guest favourite
Home in Wintergreen Resort
Wood-burning fireplace on the golf course
3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 187 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
4.95 out of 5 average rating, 176 reviews
Guest favourite
Home in Nellysford
Mountain Bauhaus with a fire pit
4 bedrooms, 2.5 bathrooms
19–24 Jul
4.9 out of 5 average rating, 128 reviews
Guest favourite
Flat in Wintergreen Resort
Deck on the golf course, wood fireplace
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.86 out of 5 average rating, 105 reviews
Guest favourite
Home in Wintergreen Resort
Eclectic mountain home near Wintergreen Resort
4 bedrooms, 6 beds, 3 bathrooms
16–21 Jul
4.95 out of 5 average rating, 239 reviews
Top guest favourite
Home in Afton
Octagonal house with 180-degree mountain views
2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
4.99 out of 5 average rating, 106 reviews
Guest favourite
Home in Wintergreen Resort
Mountain retreat with fireplace and fire pit
4 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
4.9 out of 5 average rating, 42 reviews
Top guest favourite
Chalet in Wintergreen Resort
Walk to ski with a private hot tub
3 bedrooms, 6 beds, 2.5 bathrooms
15–20 Jul
4.92 out of 5 average rating, 128 reviews
Guest favourite
Townhouse in Wintergreen Resort
Wood-burning fireplace, walk to Wintergreen resort
3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
4.9 out of 5 average rating, 83 reviews
Top guest favourite
Home in Wintergreen Resort
Wood-burning fireplace and a deck fire pit
4 bedrooms, 7 beds, 3.5 bathrooms
18–23 Jul
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
16–21 Jul
5.0 out of 5 average rating, 89 reviews
Guest favourite
Cabin in Wintergreen Resort
Double-height great room with a hot tub
5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Wintergreen Resort
Ski-in ski-out on Eagle Swoop
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 16 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
5–10 Aug
4.92 out of 5 average rating, 207 reviews
Apartment in Wintergreen Resort
Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
4.84 out of 5 average rating, 169 reviews
Top guest favourite
Bungalow in Afton
Remodeled, steps from Veritas Vineyard
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.99 out of 5 average rating, 247 reviews