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Search results; Over 1,000 homes

Guest favourite
Apartment in Wintergreen Resort
All-Season 2bd/2ba next to Spa view of Golf Course
2 bedrooms, 5 beds, 2 private bathrooms
13–18 Jul
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4.95 out of 5 average rating, 154 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.94 out of 5 average rating, 187 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 175 reviews
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
16–21 Jul
4.92 out of 5 average rating, 207 reviews
Top guest favourite
Apartment in Wintergreen Resort
2-min drive to resort, Outdoor HOA pool now open!
2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
4.97 out of 5 average rating, 175 reviews
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 30 reviews
Superhost
Home in Afton
Rockwell Ridge | Garden Suite with Full Kitchen
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
New place to stay
Home in Wintergreen Resort
True Ski-in / Ski-Out, Slopeside House
3 bedrooms, 7 beds, 2 bathrooms
11–16 Jul
New place to stay
Guest favourite
Apartment in Wintergreen Resort
Cozy Condo on the mountain at Wintergreen!
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.87 out of 5 average rating, 133 reviews
Top guest favourite
Home in Wintergreen Resort
Close to hiking! | King Beds | Fireplace | Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
23–28 Jul
4.99 out of 5 average rating, 174 reviews
Guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
4 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 89 reviews
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
3 bedrooms, 6 beds, 2 bathrooms
11–16 Jul
4.9 out of 5 average rating, 83 reviews
Top guest favourite
Bungalow in Afton
The Bungalow at Afton Mountain Retreat by Veritas
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.99 out of 5 average rating, 247 reviews
Top guest favourite
Home in Wintergreen Resort
Ski-in ski out!
2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
4.88 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Wintergreen Resort
Wintergreen Resort King bed, Fire place, 2 Bd/2 Br
2 bedrooms, 2 beds, 2 bathrooms
13–18 Jul
4.98 out of 5 average rating, 121 reviews
Guest favourite
Cabin in Wintergreen Resort
The Honey Den - Your WTG Summer Retreat! w/ Mtn Vs
5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Afton
Mountain Homestead - Hottub, King, Dogs, Gameroom
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
4.97 out of 5 average rating, 74 reviews