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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Beautiful Mountain Getaway - Walk to Everything!
3 bedrooms, 5 beds, 2 private bathrooms
6–11 Aug
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4.97 out of 5 average rating, 99 reviews
Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
4.98 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4.9 out of 5 average rating, 128 reviews, 4 bedrooms, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Sleeps 12 • Breweries
4.91 out of 5 average rating, 45 reviews, 4 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
Guest favourite
Apartment in Wintergreen Resort
Cozy Comfort with a View - Wintergreen Resort
4.91 out of 5 average rating, 165 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
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
2–7 Aug
Guest favourite
Cabin in Wintergreen Resort
Hot Tub & Views | Mid Century Modern Wonder
4.9 out of 5 average rating, 115 reviews, 5 bedrooms, 10 beds, 4.5 bathrooms
24–29 Aug
Top guest favourite
Townhouse in Wintergreen Resort
Stylish Retreat Near Trails & Tastings
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
4.96 out of 5 average rating, 270 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Apartment in Wintergreen Resort
Panoramic Sunsets Mountain Views Pool $99 Midweek
4.99 out of 5 average rating, 274 reviews, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Home in Wintergreen Resort
True Ski-in / Ski-Out, Slopeside House
New place to stay, 3 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Wintergreen Resort
Wintergreen Condo Ski In Ski Out
4.93 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
5.0 out of 5 average rating, 91 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Home in Wintergreen Resort
Designer Home w/ Incredible Views, Sleeps 16
4.94 out of 5 average rating, 102 reviews, 6 bedrooms, 9 beds, 3.5 bathrooms
15–20 Aug
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
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
4.94 out of 5 average rating, 191 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
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
1–6 Aug
Top guest favourite
Apartment in Wintergreen Resort
WonderfulViews/WalktoResort&Hiking/SpaciousCondo
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug