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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds, 3 private bathrooms
12–17 Jul
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4.99 out of 5 average rating, 183 reviews
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
12–17 Jul
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
4.95 out of 5 average rating, 175 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 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
12–17 Jul
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
4.92 out of 5 average rating, 207 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Jul
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
4.92 out of 5 average rating, 128 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4.9 out of 5 average rating, 127 reviews, 4 bedrooms, 2.5 bathrooms
12–17 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
Flat in Wintergreen Resort
Walk to Market/Slopes!
4.86 out of 5 average rating, 132 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 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
13–18 Jul
Guest favourite
Cabin in Wintergreen Resort
Hot Tub & Views | Mid Century Modern Wonder
4.9 out of 5 average rating, 114 reviews, 5 bedrooms, 10 beds, 4.5 bathrooms
18–23 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
18–23 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
13–18 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
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
12–17 Jul
Guest favourite
Apartment in Wintergreen Resort
All-Season 2bd/2ba next to Spa view of Golf Course
4.95 out of 5 average rating, 154 reviews, 2 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4.88 out of 5 average rating, 33 reviews, 4 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Home in Wintergreen Resort
Close to hiking! | King Beds | Fireplace | Hot Tub
4.99 out of 5 average rating, 174 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Aug
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