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Top guest favourite
Apartment in Wintergreen Resort
All-Season 2bd/2ba next to Spa view of Golf Course
2 bedrooms, 5 beds, 2 private bathrooms
13–18 Sept
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4.95 out of 5 average rating, 157 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
4.99 out of 5 average rating, 185 reviews
Top guest favourite
Home in Wintergreen Resort
Hottub Ski InOut Renovated Chalet Lower Tyro Slope
3 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 238 reviews
Top guest favourite
Home in Wintergreen Resort
Top of the Mountain Hideaway with Hot Tub!
3 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Wintergreen Resort
Mid-Century Escape • Sleeps 10 • Breweries
4 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Wintergreen Resort
Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!
5 bedrooms, 8 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Sept
4.92 out of 5 average rating, 130 reviews
Top guest favourite
Home in Wintergreen Resort
Amazing Views | Hot Tub | 15 mins to Wineries
4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
4.96 out of 5 average rating, 50 reviews
Home in Wintergreen Resort
Sunset Views, Hot Tub, and Firepit in Wintergreen!
5 bedrooms, 6 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Wintergreen Resort
Wintergreen 5BR | Hot Tub | Sauna | Firepit
5 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Apartment in Wintergreen Resort
Recently updated - views of the Blue Ridge Mtns
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Apartment in Wintergreen Resort
Panoramic Blue Ridge Views, Dog Retreat
2 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 87 reviews
Guest favourite
Home in Wintergreen Resort
Mountain Views in Wintergreen
5 bedrooms, 10 beds, 3.5 bathrooms
12–17 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Wintergreen Resort
Wintergreen Luxury, Breathtaking Views
6 bedrooms, 7 beds, 4.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Apartment in Wintergreen Resort
Luxury Condo in the Sky! Finest in Wintergreen!
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Home in Wintergreen Resort
Perfect House
2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 47 reviews
Guest favourite
Home in Wintergreen Resort
Designer Home w/ Incredible Views, Sleeps 16
6 bedrooms, 9 beds, 3.5 bathrooms
11–16 Oct
4.94 out of 5 average rating, 107 reviews
Guest favourite
Home in Wintergreen Resort
Hot Tub Valley View Pool Tennis Dogs OK EV Charger
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.98 out of 5 average rating, 88 reviews