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Top guest favourite
Home in Wintergreen Resort
Cliffs Edge - It’s Pumpkin Spice Time!
3 bedrooms, 4 beds, 3 shared bathrooms
26–31 Oct
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4.97 out of 5 average rating, 130 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
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
Mid-Century Escape • Sleeps 10 • Breweries
4 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
4.92 out of 5 average rating, 49 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
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
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
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
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
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
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
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
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
Apartment in Wintergreen Resort
Condo with Valley Views!
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.92 out of 5 average rating, 39 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
Top guest favourite
Home in Wintergreen Resort
Luxury home Game room Sauna, Hot Tub, Pets Welcome
4 bedrooms, 12 beds, 3.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Wintergreen Resort
Panoramic Sunsets Mountain Views Pool $99 Midweek
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Nov
4.99 out of 5 average rating, 276 reviews
Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 67 reviews