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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Extremely private, 2-min drive to skiing/hiking
2 bedrooms, 4 beds, 2 private bathrooms
12–17 Oct
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4.97 out of 5 average rating, 181 reviews
Townhouse in Wintergreen Resort
Wintergreen home, ideal location, dogs welcome!
2 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 214 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 180 reviews
Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 170 reviews
Top guest favourite
Apartment in Wintergreen Resort
Wintergreen Mountain Views - Diamond in the Slopes
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Townhouse in Wintergreen Resort
Hike*Spacious MtnTop Escape *4 EnSuites* Dogs OK
4 bedrooms, 6 beds, 4.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 216 reviews
Top guest favourite
Apartment in Wintergreen Resort
WonderfulViews/FallFoliage/Hiking/SpaciousCondo
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 54 reviews
Guest favourite
Apartment in Wintergreen Resort
BlueRidge Getaway- Dog Friendly
3 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.93 out of 5 average rating, 198 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 91 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.99 out of 5 average rating, 185 reviews
Top guest favourite
Townhouse in Wintergreen Resort
Beary Lazy - 4 beds and 2 sleeping sofas!
2 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Chalet in Wintergreen Resort
5 beds/3 BR/2 BA, Chipmunk Chase at Wintergreen
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 68 reviews
Superhost
Apartment in Wintergreen Resort
Tips Up: Cozy Slopeside Retreat w/ Fireplace
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 224 reviews
Guest favourite
Townhouse in Wintergreen Resort
King Bed Pool Tennis Golf Hiking DogOK Pack n Play
3 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
4.92 out of 5 average rating, 83 reviews
Guest favourite
Home in Wintergreen Resort
Wintergreen Condo Ski In Ski Out
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5 bedrooms, 11 beds, 4.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Rockfish
Blue Ridge Bliss - For family & friends to enjoy!
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.98 out of 5 average rating, 232 reviews