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Search results; Over 1,000 homes in Wintergreen Resort

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Guest favourite
Cabin in Wintergreen Resort
Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike
7 bedrooms, 9 beds, 6.5 private bathrooms
11–16 Oct
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4.92 out of 5 average rating, 145 reviews
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Superhost
Cabin in Wintergreen Resort
Tales from the Treehouse: Relax, Gather, Explore
4 bedrooms, 5 beds, 3 bathrooms
2–7 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
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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Home in Wintergreen Resort
Merryland with Wintergreen Advantage
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Oct
New place to stay
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Superhost
Tiny home in Afton
Luxury Treehouse • 151 Brew/WineTrail • King Bed
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
New place to stay
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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
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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Superhost
Flat in Wintergreen Resort
Eagle’s Nest @ Wintergreen
2 bedrooms, 2 queen beds, 2 bathrooms
30 Oct – 4 Nov
New place to stay
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Top guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
4.95 out of 5 average rating, 239 reviews
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Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.99 out of 5 average rating, 185 reviews
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Top guest favourite
Cottage in Wintergreen Resort
Cozy 3BR/2BR+Fire table+Foosball
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 82 reviews
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Top guest favourite
Home in Wintergreen Resort
Summit Serenity - Walk To Slopes and Restaurants
4 bedrooms, 9 beds, 3 bathrooms
24–29 Oct
4.93 out of 5 average rating, 30 reviews
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Superhost
Flat in Wintergreen Resort
Mtn Views at Swoopside Perch: Gather+Relax+Explore
3 bedrooms, 4 beds, 2 bathrooms
2–7 Oct
New place to stay
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Guest favourite
Home in Nellysford
Charming Wintergreen resort home
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
4.88 out of 5 average rating, 33 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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Home in Wintergreen Resort
Ridge View Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in Wintergreen Resort
3BR condo steps from the slopes and Inn! King Bed!
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 46 reviews
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Superhost
Home in Wintergreen Resort
Walk to Ski Slopes | Hot Tub | Fire Pit
3 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
New place to stay