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
27 Jul – 1 Aug
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4.97 out of 5 average rating, 124 reviews
Superhost
Home in Wintergreen Resort
Home in Wintergreen Resort 5BR/ 3 lvl
5 bedrooms, 7 beds, 4 bathrooms
2–7 Jul
4.91 out of 5 average rating, 81 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 186 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
Guest favourite
Flat in Wintergreen Resort
Wintergreen Getaway
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.85 out of 5 average rating, 102 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
4.9 out of 5 average rating, 83 reviews
Guest favourite
Home in Wintergreen Resort
King Bed Movie Room Fire Pit Pool Tennis Golf Hike
4 bedrooms, 7 beds, 3.5 bathrooms
12–17 Jul
4.9 out of 5 average rating, 40 reviews
Superhost
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, 204 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
1–6 Jul
4.92 out of 5 average rating, 127 reviews
Top guest favourite
Home in Wintergreen Resort
Hottub Ski InOut Renovated Chalet Lower Tyro Slope
3 bedrooms, 7 beds, 2 bathrooms
12–17 Jul
4.97 out of 5 average rating, 233 reviews
Guest favourite
Cabin in Wintergreen Resort
Bide-a-Wee- Hike the Trails! Close to the slopes!
3 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
4.87 out of 5 average rating, 61 reviews
Top guest favourite
Home in Nellysford
Glass & Pine, close to Bold Rock & Vineyards
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Afton
Mountain Overlook House - Blue Ridge Parkway
2 bedrooms, 2 beds, 2 bathrooms
10–15 Jul
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
3 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5 bedrooms, 11 beds, 4.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 13 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
Superhost
Apartment in Wintergreen Resort
Your Cozy Mountain Getaway Awaits
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.79 out of 5 average rating, 107 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, 181 reviews