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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
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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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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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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Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.94 out of 5 average rating, 196 reviews
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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
Perfect House
2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.98 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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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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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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Guest favourite
Apartment in Wintergreen Resort
Ski-in/Ski-out Wintergreen Highlands Condo -Views!
2 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
4.95 out of 5 average rating, 201 reviews
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Guest favourite
Flat in Wintergreen Resort
Condo Atop Wintergreen Resort, Easy Walk To Slope
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 8 reviews
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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
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
Cabin in Shipman
Wellness Cabin Retreat w/ Sauna, Hot Tub & Library
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
New place to stay
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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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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