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Search results; Over 1,000 homes in Greenwood

Top guest favourite
Home in Greenwood
Gorgeous Modern Mountain Home + Blue Ridge Views
3 bedrooms, 3 beds, 2.5 private bathrooms
23–28 Aug
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5.0 out of 5 average rating, 239 reviews
Guest favourite
Bungalow in Waynesboro
Cheerful 2 bd bungalow with HOT TUB! Pet friendly!
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 397 reviews
Guest favourite
Cabin in Afton
Afton Mountain Retreat - The Cabin
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.91 out of 5 average rating, 76 reviews
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 271 reviews
Superhost
Home in Crozet
Blairbrook Farm | Spacious Retreat Near Vineyards
4 bedrooms, 7 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Home in Afton
Wine Country Retreat Near National Park
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Tiny home in Faber
The Stilt House at Perkins Hollow
1 bedroom, 1 bed, 1 bathroom
7–12 Aug
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Treehouse in Stanardsville
CloudPointe Retreat
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 122 reviews
Guest favourite
Cabin in Waynesboro
Vintage Log Cabin close to wineries & hiking
3 bedrooms, 3 queen beds, 1 bathroom
7–12 Aug
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Guest house in Charlottesville
Historic HomeTract Cottage UVA/Charlottesville/Ivy
1 bedroom, 2 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Cottage in Nelson County
Starlit Soak – Romantic Hideaway in the Hollow
2 king beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Afton
Farmhouse on 151 w/ Firepit, Huge Yard, Mtn Views
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.93 out of 5 average rating, 147 reviews
Guest favourite
Cottage in Afton
GreenHouseNelson
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
4.87 out of 5 average rating, 512 reviews
Superhost
Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Aug
Superhost
Cottage in Crozet
Idyllic Cottage Retreat
2 bedrooms, 1 bathroom
1–6 Dec
4.89 out of 5 average rating, 257 reviews
Top guest favourite
Flat in Crozet
Mtn Vineyards Getaway
1 bedroom, 2 beds, 1 bathroom
7–12 Aug
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Dyke
Cozy Cabin w/ Hot Tub & EV Charger near Shenandoah
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Charlottesville
The Ivy Rose Tea House, 15 min to Cville & Mtns
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Aug
4.93 out of 5 average rating, 153 reviews