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Search results; Over 1,000 homes

Top guest favourite
Home in Wintergreen Resort
Cliffs Edge -A Contemporary Mountain Home
3 bedrooms, 4 beds, 3 shared bathrooms
10–15 Aug
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4.97 out of 5 average rating, 125 reviews
Guest favourite
Chalet in Wintergreen Resort
Owl Bnb | Walkable to Slopes | Speakeasy Room
4.94 out of 5 average rating, 187 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
4.95 out of 5 average rating, 175 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Superhost
Home in Afton
Rockwell Ridge | Garden Suite with Full Kitchen
New place to stay, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
4.92 out of 5 average rating, 207 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Jul
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Home in Wintergreen Resort
Cozy Wintergreen Townhome
4.96 out of 5 average rating, 27 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
11–16 Jul
Guest favourite
Home in Wintergreen Resort
Designer Look: Mountain View Pool Tennis One Level
4.88 out of 5 average rating, 33 reviews, 4 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
4.97 out of 5 average rating, 265 reviews, 2 bedrooms, 3 beds, 1 bathroom
29 Jul – 3 Aug
Guest favourite
Chalet in Wintergreen Resort
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
4.89 out of 5 average rating, 36 reviews, 4 bedrooms, 8 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Chalet in Wintergreen Resort
Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK
4.94 out of 5 average rating, 62 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
Top guest favourite
Apartment in Wintergreen Resort
2-min drive to resort, Outdoor HOA pool now open!
4.97 out of 5 average rating, 175 reviews, 2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Guest favourite
Cabin in Wintergreen Resort
The Honey Den - Your WTG Summer Retreat! w/ Mtn Vs
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
15–20 Jul
Top guest favourite
Chalet in Wintergreen Resort
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
4.92 out of 5 average rating, 128 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Jul
Guest favourite
Townhouse in Wintergreen Resort
Cozy condo with loft. Walk to Wintergreen resort!
4.9 out of 5 average rating, 83 reviews, 3 bedrooms, 6 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Home in Wintergreen Resort
Ski-in ski out!
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Jul
Top guest favourite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
5.0 out of 5 average rating, 89 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
4.9 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Superhost
Apartment in Wintergreen Resort
Fox Paw | Walk to Slopes & Village at Wintergreen
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul