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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Breathtaking Views from The Ledges
3 bedrooms, 6 beds, 3 private bathrooms
4–9 Aug
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4.98 out of 5 average rating, 52 reviews
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Sleeps 12 • Breweries
4 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
4.91 out of 5 average rating, 45 reviews
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 271 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.94 out of 5 average rating, 192 reviews
Guest favourite
Cabin in Wintergreen Resort
Hot Tub & Views | Mid Century Modern Wonder
5 bedrooms, 10 beds, 4.5 bathrooms
24–29 Aug
4.9 out of 5 average rating, 115 reviews
Guest favourite
Cabin in Wintergreen Resort
3 Levels · 3 Scenic Decks · Game Room · Hot Tub
5 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
4.97 out of 5 average rating, 118 reviews
Guest favourite
Home in Wintergreen Resort
Home Outdoor Fire Pit Arcade, Scenic Helipad Views
3 bedrooms, 7 beds, 3.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 8 reviews
Home in Afton
The Cupola Creek House
4 bedrooms, 8 beds, 3 bathrooms
4–9 Aug
New place to stay
Top guest favourite
Chalet in Wintergreen Resort
5 beds/3 BR/2 BA, Chipmunk Chase at Wintergreen
3 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
4.94 out of 5 average rating, 68 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 177 reviews
Guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds, 3 bathrooms
5–10 Aug
4.95 out of 5 average rating, 239 reviews
Top guest favourite
Home in Afton
Mountain Overlook House - Blue Ridge Parkway
2 bedrooms, 2 beds, 2 bathrooms
13–18 Aug
4.99 out of 5 average rating, 106 reviews
Guest favourite
Townhouse in Wintergreen Resort
Wintergreen home, ideal location, dogs welcome!
2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 214 reviews
Top guest favourite
Treehouse in Roseland
Blue Ridge Treehouse
1 bedroom, 1 king bed, 1 bathroom
4–9 Aug
4.93 out of 5 average rating, 85 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
14–19 Aug
4.92 out of 5 average rating, 213 reviews
Top guest favourite
Home in Wintergreen Resort
Perfect House
2 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5 bedrooms, 11 beds, 4.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cabin in Wintergreen Resort
The Honey Den - Your WTG Summer Retreat! w/ Mtn Vs
5 bedrooms, 7 beds, 4.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 6 reviews