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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
20–25 Jul
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4.97 out of 5 average rating, 125 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
18–23 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
18–23 Jul
Top guest favourite
Bungalow in Afton
The Bungalow at Afton Mountain Retreat by Veritas
4.99 out of 5 average rating, 248 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
4.92 out of 5 average rating, 209 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Aug
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
4.91 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Townhouse in Wintergreen Resort
Beary Lazy - 4 beds and 2 sleeping sofas!
5.0 out of 5 average rating, 66 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
4.9 out of 5 average rating, 84 reviews, 3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
Guest favourite
Townhouse in Wintergreen Resort
4BR (3 KING)+ Shuffleboard + Hot Tub + EV Outlet
4.94 out of 5 average rating, 99 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
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
17–22 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
7–12 Aug
Top guest favourite
Apartment in Wintergreen Resort
Five Minute Walk to Everything!
4.96 out of 5 average rating, 358 reviews, 2 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Wintergreen Resort
The Bears Perch Cabin -Private Hottub and Sauna
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
20–25 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
17–22 Jul
Guest favourite
Home in Wintergreen Resort
Hot Tub Valley View Pool Tennis Dogs OK EV Charger
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
Superhost
Flat in Wintergreen Resort
Ski-In/Ski-Out + Blue Ridge Views | Wintergreen
New place to stay, 3 bedrooms, 4 beds, 3 bathrooms
19–24 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
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