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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Panoramic Sunsets Mountain Views Pool $99 Midweek
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Aug
,
4.99 out of 5 average rating, 274 reviews
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
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
Chalet in Wintergreen Resort
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
4.89 out of 5 average rating, 36 reviews, 4 bedrooms, 8 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Near Breweries • Sleeps 12
4.9 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Apartment in Wintergreen Resort
2-min drive to resort, Outdoor HOA pool now open!
4.97 out of 5 average rating, 175 reviews, 2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
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
12–17 Jul
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4.9 out of 5 average rating, 126 reviews, 4 bedrooms, 2.5 bathrooms
12–17 Jul
Guest favourite
Chalet in Wintergreen Resort
Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK
4.94 out of 5 average rating, 62 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
Top guest favourite
Apartment in Wintergreen Resort
What-a-Mountain View Pool Tennis Hike Golf KingBed
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 6 beds, 3 bathrooms
18–23 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
11–16 Jul
Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
4.95 out of 5 average rating, 161 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
Guest favourite
Apartment in Wintergreen Resort
Condo with Valley Views!
4.93 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Wintergreen Resort
King Bed Movie Room Fire Pit Pool Tennis Golf Hike
4.9 out of 5 average rating, 41 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
12–17 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
Top guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5.0 out of 5 average rating, 15 reviews, 5 bedrooms, 11 beds, 4.5 bathrooms
11–16 Jul
Guest favourite
Flat in Wintergreen Resort
Cozy Wintergreen Retreat | Fireplace + Pool
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 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
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
11–16 Jul