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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
8–13 Nov
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5.0 out of 5 average rating, 242 reviews
Guest favourite
Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Afton
Farmhouse on Working Vineyard
5 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.94 out of 5 average rating, 163 reviews
Top guest favourite
Home in Crozet
Forest Zen: near vineyards/Shenandoah Nat’l park
5 bedrooms, 5 king beds, 6.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 87 reviews
Guest favourite
Home in Afton
Farmhouse on 151 w/ Firepit, Huge Yard, Mtn Views
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 149 reviews
Top guest favourite
Guest house in Crozet
Elegant and Convenient in Crozet
1 bedroom, 1 queen bed, 1 bathroom
3–8 Oct
4.98 out of 5 average rating, 586 reviews
Superhost
Home in Waynesboro
7BR Sleeps 20 | Hot Tub | Cville & Blue Ridge Pkwy
7 bedrooms, 10 beds, 3 bathrooms
18–23 Sept
New place to stay
Top guest favourite
Home in Charlottesville
6-Acre Escape Near UVA & Wineries! King Suite
4 bedrooms, 9 beds, 3.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Home in Crozet
4BR Farm Stay Pool, Hot Tub, Wine Country
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 58 reviews
Guest favourite
Home in Charlottesville
Casa Crozet
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Waynesboro
Scenic Blue Ridge Sanctuary
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.93 out of 5 average rating, 254 reviews
Guest favourite
Cottage in Afton
The Cottage @ Afton Mountain- Close to Wineries!
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 306 reviews
Top guest favourite
Cottage in Charlottesville
The Peony Cottage in Charlottesville
2 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Home in Afton
Glass Hollow Get-away
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Waynesboro
Cute Place in Waynesboro
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Afton
Lewis Catherine House
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 176 reviews
Top guest favourite
Home in Afton
Perfect getaway among the orchards of Batesville
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 126 reviews
Home in Charlottesville
Modern Farmhouse w/POOL. Work Retreat.
3 bedrooms, 4 beds, 2 bathrooms
28 Oct – 2 Nov
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Greenwood
Private Carriage House, close to Shenandoah & 151
1 bedroom, 1 bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 71 reviews