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Search results; Over 1,000 homes

Guest favourite
Cabin in Wintergreen Resort
Modern Cabin with Hot tub and Sauna
5 bedrooms, 8 beds, 4.5 shared bathrooms
13–18 Sept
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4.91 out of 5 average rating, 113 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 215 reviews
Guest favourite
Townhouse in Wintergreen Resort
King Bed Pool Tennis Golf Hiking DogOK Pack n Play
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.92 out of 5 average rating, 83 reviews
Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 168 reviews
Guest favourite
Home in Wintergreen Resort
Renovated 4+BR luxury townhome @ the Mountain Top!
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.89 out of 5 average rating, 64 reviews
Guest favourite
Flat in Wintergreen Resort
Fantastic views/FallFoliage/PupFriendly!
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Wintergreen Resort
Extremely private, HOA pool/stair-free entry
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 180 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.91 out of 5 average rating, 85 reviews
Top guest favourite
Apartment in Wintergreen Resort
Beautiful Mountain Getaway - Walk to Everything!
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 100 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 180 reviews
Apartment in Wintergreen Resort
Wintergreen Condo w/ Pool: Near Hike & Market!
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 29 reviews
Townhouse in Wintergreen Resort
Wintergreen home, ideal location, dogs welcome!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.91 out of 5 average rating, 214 reviews
Top guest favourite
Apartment in Wintergreen Resort
WonderfulViews/FallFoliage/Hiking/SpaciousCondo
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Wintergreen Resort
Perfect House
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 47 reviews
Chalet in Roseland
Sleepy Bear Chalet
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.62 out of 5 average rating, 140 reviews
Guest favourite
Apartment in Roseland
Great location! Steps from dining/ event spaces!
1 bedroom, 2 double beds, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 34 reviews
Superhost
Apartment in Wintergreen Resort
Your Cozy Mountain Getaway Awaits
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.8 out of 5 average rating, 109 reviews
Townhouse in Wintergreen Resort
Southampton @ Wintergreen Resort
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Wintergreen Resort
What-a-Mountain View Pool Tennis Hike Golf KingBed
3 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 51 reviews