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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
10–15 Aug
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4.97 out of 5 average rating, 125 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, 187 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
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4 bedrooms, 2.5 bathrooms
12–17 Jul
4.9 out of 5 average rating, 126 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
16–21 Jul
4.92 out of 5 average rating, 207 reviews
Guest favourite
Cabin in Wintergreen Resort
The Honey Den - Your WTG Summer Retreat! w/ Mtn Vs
5 bedrooms, 7 beds, 4.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds, 3 bathrooms
10–15 Jul
4.95 out of 5 average rating, 238 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
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
29 Jul – 3 Aug
4.97 out of 5 average rating, 265 reviews
Superhost
Home in Afton
Rockwell Ridge | Garden Suite with Full Kitchen
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
New place to stay
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Wintergreen Resort
Ski-in ski out!
2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
4.9 out of 5 average rating, 83 reviews
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Jul
4.92 out of 5 average rating, 128 reviews
Guest favourite
Home in Wintergreen Resort
Cozy Wintergreen Townhome
4 bedrooms, 7 beds, 3.5 bathrooms
10–15 Jul
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
4.88 out of 5 average rating, 33 reviews
Guest favourite
Home in Wintergreen Resort
Swim | Hike | Fish | at Wintergreen Resort
4 bedrooms, 8 beds, 4.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 9 reviews
Home in Wintergreen Resort
True Ski-in / Ski-Out, Slopeside House
3 bedrooms, 7 beds, 2 bathrooms
9–14 Jul
New place to stay
Guest favourite
Chalet in Wintergreen Resort
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
4 bedrooms, 8 beds, 2.5 bathrooms
12–17 Jul
4.89 out of 5 average rating, 36 reviews