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Search results; Over 1,000 homes

Top guest favourite
Cabin in Wintergreen Resort
Cozy Mountain Retreat- Walk to trails-EV charger
4 bedrooms, 5 beds, 3 private bathrooms
19–24 Jul
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4.99 out of 5 average rating, 112 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
4.95 out of 5 average rating, 175 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 187 reviews
Top guest favourite
Home in Wintergreen Resort
Cozy Wintergreen Townhome
4 bedrooms, 7 beds, 3.5 bathrooms
14–19 Jul
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Wintergreen Resort
Five Minute Walk to Everything!
2 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
4.96 out of 5 average rating, 358 reviews
Top guest favourite
Apartment in Wintergreen Resort
2-min drive to resort, Outdoor HOA pool now open!
2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
4.97 out of 5 average rating, 176 reviews
Guest favourite
Flat in Wintergreen Resort
Cozy Wintergreen Retreat | Fireplace + Pool
2 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 25 reviews
Guest favourite
Flat in Wintergreen Resort
Laurelwood Hollow: Walk to Ski & Swim
2 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
14–19 Jul
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds, 3 bathrooms
14–19 Jul
4.95 out of 5 average rating, 239 reviews
Guest favourite
Home in Nellysford
Mountain Bauhaus | Sleeps 8 | Amenities | Grill
4 bedrooms, 2.5 bathrooms
19–24 Jul
4.9 out of 5 average rating, 127 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Jul
4.9 out of 5 average rating, 83 reviews
Top guest favourite
Home in Roseland
The Treehouse at Wintergreen
4 bedrooms, 8 beds, 3 bathrooms
14–19 Jul
4.94 out of 5 average rating, 85 reviews
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Townhouse in Wintergreen Resort
Stylish Retreat Near Trails & Tastings
3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Chalet in Wintergreen Resort
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
4 bedrooms, 8 beds, 2.5 bathrooms
14–19 Jul
4.89 out of 5 average rating, 37 reviews
Top guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5 bedrooms, 11 beds, 4.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Wintergreen Resort
Mountain Views
2 bedrooms, 3 beds, 2 bathrooms
18–23 Jul
4.77 out of 5 average rating, 174 reviews
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Near Breweries • Sleeps 12
4 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
4.91 out of 5 average rating, 43 reviews