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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
5–10 Jul
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4.99 out of 5 average rating, 272 reviews
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
5–10 Jul
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4.88 out of 5 average rating, 32 reviews, 4 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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
Top guest favourite
Apartment in Wintergreen Resort
Spacious Ski In Ski Out Condo with Mountain View
5.0 out of 5 average rating, 42 reviews, 2 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
Top guest favourite
Apartment in Wintergreen Resort
Beautiful Mountain Getaway - Walk to Everything!
4.97 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
4.98 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Superhost
Apartment in Wintergreen Resort
Amazing property, near to Slopes & Dogs OK
4.76 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
Townhouse in Wintergreen Resort
Southampton @ Wintergreen Resort
4.73 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Jul
Top guest favourite
Apartment in Wintergreen Resort
2-min drive to resort, Outdoor HOA pool now open!
4.97 out of 5 average rating, 173 reviews, 2 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
4.94 out of 5 average rating, 186 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4.95 out of 5 average rating, 238 reviews, 4 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
Guest favourite
Home in Wintergreen Resort
Entire Home at Wintergreen Resort - Bear Pause
4.92 out of 5 average rating, 12 reviews, 5 bedrooms, 8 beds, 2.5 bathrooms
1–6 Jul
Guest favourite
Flat in Wintergreen Resort
Cozy Wintergreen Retreat | Fireplace + Pool
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 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, 41 reviews, 4 bedrooms, 7 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Wintergreen Resort
Mountain View | Hot tub | Sleeps 14
5.0 out of 5 average rating, 14 reviews, 5 bedrooms, 11 beds, 4.5 bathrooms
5–10 Jul
Top guest favourite
Home in Wintergreen Resort
Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
4.89 out of 5 average rating, 158 reviews, 5 bedrooms, 9 beds, 4 bathrooms
21–26 Jul
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
5.0 out of 5 average rating, 88 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
4–9 Jul
Guest favourite
Home in Wintergreen Resort
Cozy Wintergreen Townhome
4.96 out of 5 average rating, 26 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
7–12 Jul