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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Panoramic Sunsets Mountain Views Pool $99 Midweek
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Aug
,
4.99 out of 5 average rating, 274 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
4.95 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Jul
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4.9 out of 5 average rating, 128 reviews, 4 bedrooms, 2.5 bathrooms
19–24 Jul
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
4.94 out of 5 average rating, 187 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
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
17–22 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
16–21 Jul
Top guest favourite
Home in Afton
Mountain Overlook House - Blue Ridge Parkway
4.99 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
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
16–21 Jul
Guest favourite
Flat in Wintergreen Resort
Cozy Wintergreen Retreat | Fireplace + Pool
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
5.0 out of 5 average rating, 89 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
17–22 Jul
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
4.92 out of 5 average rating, 208 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Aug
Top guest favourite
Home in Wintergreen Resort
Ski-in ski out!
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Jul
Top guest favourite
Bungalow in Afton
The Bungalow at Afton Mountain Retreat by Veritas
4.99 out of 5 average rating, 247 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Guest favourite
Cabin in Wintergreen Resort
The Honey Den - Your WTG Summer Retreat! w/ Mtn Vs
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Jul
Top guest favourite
Cabin in Vesuvius
The Sanctuary
4.99 out of 5 average rating, 374 reviews, 2 bedrooms, 5 beds, 2.5 bathrooms
16–21 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
20–25 Jul
Guest favourite
Home in Wintergreen Resort
King Bed Movie Room Fire Pit Pool Tennis Golf Hike
4.9 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
Superhost
Home in Roseland
On Mountain Time: NEW house near Devil's Backbone
New place to stay, 5 bedrooms, 6 beds, 3.5 bathrooms
17–22 Jul