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Search results; Over 1,000 homes

Guest favourite
Apartment in Wintergreen Resort
Panoramic Peak: Wintergreen Condo with Views
1 bedroom, 2 beds, 2 private bathrooms
25–30 Aug
,
4.9 out of 5 average rating, 155 reviews
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
Superhost
Campsite in Afton
Parking Spot for RV with water/electric
1 bed
20–25 Aug
Superhost
Home in Wintergreen Resort
Ski Chalet | Walk to Slopes | Hot Tub
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
New place to stay
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
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
Top guest favourite
Flat in Wintergreen Resort
Cozy Wintergreen Retreat | Fireplace + Pool
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 31 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
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
Guest favourite
Cabin in Nellysford
Tiny Luxury Retreat: Lake, Hikes, Brews & Vines
2 bedrooms, 1 king bed, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 281 reviews
Home in Wintergreen Resort
Cozy Condo | 2BR Family-Friendly for 6 | Ski, Hike
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
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
Guest favourite
Apartment in Wintergreen Resort
Ski-In Ski-Out ~ Mtn Views ~ King Suite
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
4.95 out of 5 average rating, 179 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
Top guest favourite
Farm stay in Afton
Afton, Mountain View Mini Farm
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 347 reviews
Top guest favourite
Apartment in Wintergreen Resort
Extremely private, HOA pool/stair-free entry
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.97 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, 196 reviews
Superhost
Home in Wintergreen Resort
Hillside Hideaway
3 bedrooms, 4 beds, 3.5 bathrooms
24–29 Aug
4.84 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Wintergreen Resort
Panoramic Blue Ridge Views | dog friendly | pools!
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 23 reviews