filters

Search results; Over 1,000 homes

Photo 1 of 29
Top guest favourite
Apartment in Wintergreen Resort
Extremely private, 2-min drive to skiing/hiking
2 bedrooms, 4 beds, 2 private bathrooms
26–31 Oct
,
4.97 out of 5 average rating, 182 reviews
Photo 1 of 29
Superhost
Flat in Wintergreen Resort
Swoopside Perch: Gather+Relax+Explore w/ Mtn Views
3 bedrooms, 4 beds, 2 bathrooms
2–7 Oct
New place to stay
Photo 1 of 29
Home in Wintergreen Resort
Breathing Room
5 bedrooms, 6 beds, 3.5 bathrooms
18–23 Sept
New place to stay
Photo 1 of 20
Top guest favourite
Apartment in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
3 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.99 out of 5 average rating, 185 reviews
Photo 1 of 29
Guest favourite
Home in Wintergreen Resort
Wintergreen Ridgeline Retreat
2 bedrooms, 4 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Wintergreen Resort
Bear's Mountain Escape
3 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
4.95 out of 5 average rating, 170 reviews
Photo 1 of 29
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
Photo 1 of 19
Top guest favourite
Apartment in Wintergreen Resort
Where the Trail Ends
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.93 out of 5 average rating, 257 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Chalet in Wintergreen Resort
5 beds/3 BR/2 BA, Chipmunk Chase at Wintergreen
3 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
4.94 out of 5 average rating, 69 reviews
Photo 1 of 11
Guest favourite
Apartment in Roseland
Great location! Steps from dining/ event spaces!
1 bedroom, 2 double beds, 1 bathroom
18–23 Sept
4.91 out of 5 average rating, 34 reviews
Photo 1 of 15
Guest favourite
Apartment in Wintergreen Resort
Your Cozy Mountain Getaway Awaits
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.8 out of 5 average rating, 109 reviews
Photo 1 of 29
Home in Wintergreen Resort
Creature Comforts
2 bedrooms, 2 beds, 2.5 bathrooms
18–23 Sept
New place to stay
Photo 1 of 29
Guest favourite
Apartment in Wintergreen Resort
Wintergreen! Dog friendly, cozy and comfortable
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.9 out of 5 average rating, 73 reviews
Photo 1 of 29
Top guest favourite
Home in Wintergreen Resort
Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!
5 bedrooms, 8 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 92 reviews
Photo 1 of 29
Top guest favourite
Flat in Rockfish
Blue Ridge Bliss - For family & friends to enjoy!
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.98 out of 5 average rating, 232 reviews
Photo 1 of 21
Guest favourite
Apartment in Wintergreen Resort
Ski-in/Ski-out Wintergreen Highlands Condo -Views!
2 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.95 out of 5 average rating, 200 reviews