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Search results; Over 1,000 homes

Top guest favourite
Home in Wintergreen Resort
Cliffs Edge -A Contemporary Mountain Home
3 bedrooms, 4 beds, 3 shared bathrooms
5–10 Aug
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4.97 out of 5 average rating, 124 reviews
Top guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
4.95 out of 5 average rating, 238 reviews
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
3 bedrooms, 6 beds, 2.5 bathrooms
6–11 Jul
4.92 out of 5 average rating, 127 reviews
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.97 out of 5 average rating, 263 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 175 reviews
Guest favourite
Cottage in Afton
Cottage on 151 w/ Hot Tub, Firepit, Mountain Views
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 184 reviews
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4 bedrooms, 2.5 bathrooms
5–10 Jul
4.9 out of 5 average rating, 126 reviews
Guest favourite
Flat in Wintergreen Resort
Wintergreen Getaway
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.85 out of 5 average rating, 103 reviews
Superhost
Apartment in Wintergreen Resort
Your Cozy Mountain Getaway Awaits
2 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
4.79 out of 5 average rating, 107 reviews
Guest favourite
Chalet in Wintergreen Resort
Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK
3 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Home in Afton
Mountain Overlook House - Blue Ridge Parkway
2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 88 reviews
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
4.9 out of 5 average rating, 83 reviews
Top guest favourite
Townhouse in Wintergreen Resort
Beary Lazy - 4 beds and 2 sleeping sofas!
2 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 66 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.94 out of 5 average rating, 186 reviews
Guest favourite
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
16–21 Jul
4.93 out of 5 average rating, 205 reviews
Guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.89 out of 5 average rating, 9 reviews