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Search results; Over 1,000 homes in Wintergreen Resort

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Top guest favourite
Apartment in Wintergreen Resort
Five Minute Walk to Everything!
2 bedrooms, 5 beds, 2 private bathrooms
31 Oct – 5 Nov
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4.96 out of 5 average rating, 365 reviews
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Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 216 reviews
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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, 48 reviews
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Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 170 reviews
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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
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Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 92 reviews
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Top guest favourite
Chalet in Wintergreen Resort
Lux Wellness|FamilyFun|HotTub Sauna Massage
6 bedrooms, 11 beds, 4 bathrooms
4–9 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.99 out of 5 average rating, 67 reviews
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Superhost
Flat in Wintergreen Resort
Eagle’s Nest @ Wintergreen
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Apartment in Wintergreen Resort
Your Cozy Mountain Getaway Awaits
2 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.8 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Wintergreen Resort
Hottub Ski InOut Renovated Chalet Lower Tyro Slope
3 bedrooms, 7 beds, 2 bathrooms
11–16 Oct
4.97 out of 5 average rating, 238 reviews
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Top guest favourite
Chalet in Wintergreen Resort
5 beds/3 BR/2 BA, Chipmunk Chase at Wintergreen
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 69 reviews
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Guest favourite
Home in Wintergreen Resort
Wintergreen Ridgeline Retreat
2 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 6 reviews
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Guest house in Nellysford
The Cozy Carriage House
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Home in Wintergreen Resort
Heaven On Earth
6 bedrooms, 13 beds, 5.5 bathrooms
11–16 Oct
4.96 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Wintergreen Resort
Coziest Condo 1st floor, walk to the Patio Terrace
1 bedroom, 1 king bed, 1 bathroom
1–6 May
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Townhouse in Wintergreen Resort
Wild Ridges - Newly Renovated!
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Mar
4.95 out of 5 average rating, 39 reviews
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Top guest favourite
Townhouse in Wintergreen Resort
Stylish Retreat Near Trails & Tastings/ ski
3 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 15 reviews
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Superhost
Cabin in Shipman
Wellness Cabin Retreat w/ Sauna, Hot Tub & Library
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
New place to stay