filters

Search results; Over 1,000 homes

Photo 1 of 19
Apartment in Wintergreen Resort
Cozy 1-bedroom Condo with Fireplace Near Ski Slope
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
,
4.75 out of 5 average rating, 102 reviews
Photo 1 of 29
Superhost
Cabin in Wintergreen Resort
Tales from a Treehouse: Relax, Gather, Explore
4 bedrooms, 5 beds
1–6 Oct
New place to stay
Photo 1 of 29
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 92 reviews
Photo 1 of 29
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds
20–25 Sept
4.92 out of 5 average rating, 216 reviews
Photo 1 of 29
Guest favourite
Townhouse in Wintergreen Resort
Wild Ridges - Newly Renovated!
4 bedrooms, 4 beds
1–6 Mar
4.95 out of 5 average rating, 39 reviews
Photo 1 of 29
Guest favourite
Home in Wintergreen Resort
Wintergreen Ridgeline Retreat
2 bedrooms, 4 beds
2–7 Nov
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Top guest favourite
Apartment in Wintergreen Resort
Condo with Valley Views!
2 bedrooms, 2 beds
21–26 Sept
4.93 out of 5 average rating, 40 reviews
Photo 1 of 26
Guest favourite
Home in Nellysford
Charming Wintergreen resort home
4 bedrooms, 4 beds
25–30 Sept
4.88 out of 5 average rating, 33 reviews
Photo 1 of 15
Guest favourite
Flat in Wintergreen Resort
Wintergreen Getaway
2 bedrooms, 3 beds
22–27 Sept
4.86 out of 5 average rating, 112 reviews
Photo 1 of 21
Guest favourite
Apartment in Wintergreen Resort
Ski-in/Ski-out Wintergreen Highlands Condo -Views!
2 bedrooms, 4 beds
15–20 Nov
4.95 out of 5 average rating, 200 reviews
Photo 1 of 20
Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds
20–25 Sept
4.99 out of 5 average rating, 185 reviews
Photo 1 of 29
Top guest favourite
Cabin in Wintergreen Resort
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 67 reviews
Photo 1 of 29
Guest favourite
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
4 bedrooms, 6 beds
21–26 Sept
4.95 out of 5 average rating, 239 reviews
Photo 1 of 22
Top guest favourite
Home in Wintergreen Resort
Blue Bear
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 13 reviews
Photo 1 of 29
Top guest favourite
Home in Wintergreen Resort
Hottub Ski InOut Renovated Chalet Lower Tyro Slope
3 bedrooms, 7 beds
20–25 Sept
4.97 out of 5 average rating, 238 reviews
Photo 1 of 29
Top guest favourite
Flat in Wintergreen Resort
little mountain haven. True ski-in Ski out
1 bedroom, 1 king bed
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Photo 1 of 21
Top guest favourite
Apartment in Wintergreen Resort
Beautiful Mountain Getaway - Walk to Everything!
3 bedrooms, 5 beds
23–28 Sept
4.97 out of 5 average rating, 100 reviews
Photo 1 of 29
Top guest favourite
Home in Wintergreen Resort
Cliffs Edge - It’s Pumpkin Spice Time!
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 130 reviews
Photo 1 of 29
Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 170 reviews