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Search results; Over 1,000 homes

Top guest favourite
Apartment in Wintergreen Resort
Extremely private, HOA pool/stair-free entry
2 bedrooms, 4 beds, 2 private bathrooms
24–29 Aug
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4.97 out of 5 average rating, 180 reviews
Home in Waynesboro
Basic City Rancher
3 bedrooms, 3 queen beds, 1 bathroom
19–24 Aug
New place to stay
Superhost
Apartment in Wintergreen Resort
1 bedroom condo, close to hikes & breweries & pool
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 214 reviews
Guest favourite
Townhouse in Wintergreen Resort
King Bed Pool Tennis Golf Hiking DogOK Pack n Play
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 82 reviews
Home in Wintergreen Resort
Wintergreen Ridgeline Retreat
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Flat in Wintergreen Resort
1BR 2BA Cozy Retreat Steps from Wintergreen Resort
1 bedroom, 3 beds, 2 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 274 reviews
Top guest favourite
Home in Wintergreen Resort
Close to hiking! | King Beds | Fireplace | Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 180 reviews
Guest favourite
Apartment in Wintergreen Resort
BlueRidge Getaway- Dog Friendly
3 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
4.93 out of 5 average rating, 195 reviews
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
4.95 out of 5 average rating, 179 reviews
Chalet in Wintergreen Resort
Alpine Ascent
3 bedrooms, 4 beds, 3 bathrooms
20–25 Aug
New place to stay
Guest favourite
Cabin in Nellysford
Tiny Luxury Retreat: Lake, Hikes, Brews & Vines
2 bedrooms, 1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 281 reviews
Guest favourite
Apartment in Wintergreen Resort
Cozy Condo on the mountain at Wintergreen!
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.88 out of 5 average rating, 136 reviews
Guest favourite
Home in Wintergreen Resort
The Fairway Chalet • Sleeps 6 • Dog Friendly
3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Room in Roseland
Private Entrance Mountain Lodge Room/Nelson Rt151
2 beds, 1 bathroom
28 Aug – 2 Sept
4.93 out of 5 average rating, 70 reviews
Apartment in Wintergreen Resort
Wintergreen Condo w/ Pool: Near Hike & Market!
2 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
4.86 out of 5 average rating, 29 reviews
Guest favourite
Apartment in Wintergreen Resort
Firefly on The Ridge: Mountain + Ski Slope Views
2 bedrooms, 2 king beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Tyro
Creekside Retreat | Fire Pit + Big Fenced Yard
3 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 312 reviews
Top guest favourite
Cabin in Tyro
Tyro Mountain View Cabin
2 bedrooms, 2 double beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 380 reviews