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Search results; Over 1,000 homes in Greenwood

Top guest favourite
Guest house in Greenwood
Private Carriage House, close to Shenandoah & 151
1 bedroom, 1 bed, 1 private bathroom
3–8 Oct
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5.0 out of 5 average rating, 71 reviews
Top guest favourite
Home in Greenwood
Gorgeous Modern Mountain Home + Blue Ridge Views
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Nov
5.0 out of 5 average rating, 242 reviews
Guest favourite
Home in Afton
Farmhouse on Working Vineyard
5 bedrooms, 6 beds, 3 bathrooms
10–15 Sept
4.94 out of 5 average rating, 162 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
Guest favourite
Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Charlottesville
6-Acre Escape Near UVA & Wineries! King Suite
4 bedrooms, 9 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 90 reviews
Guest favourite
Home in Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.93 out of 5 average rating, 243 reviews
Superhost
Chalet in Afton
Chalet house next to wineries/breweries!
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 547 reviews
Guest favourite
Home in Afton
The Hidden Plum Hollow Residence
5 bedrooms, 6 beds, 4 bathrooms
14–19 Sept
4.91 out of 5 average rating, 77 reviews
Top guest favourite
Home in Afton
26 Acres/Mtn Views/Hot Tub/Firepit/Privacy!
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Home in Crozet
Crozet Casa HotTub Fire Pit, Wine & Beer, PEACE
4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Dec
4.97 out of 5 average rating, 221 reviews
Superhost
Guest house in Crozet
Birds & Bees Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Dec
Superhost
Home in Crozet
Blairbrook Farm | Spacious Retreat Near Vineyards
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Crozet
Carter Street | Walkable Crozet | Pet-Friendly
3 bedrooms, 3 queen beds, 2 bathrooms
9–14 Sept
4.88 out of 5 average rating, 17 reviews
Home in Afton
The Cupola Creek House
4 bedrooms, 8 beds, 3 bathrooms
8–13 Sept
New place to stay
Superhost
Cottage in Afton
Fox Cottage – Modern Wine Country Retreat
2 bedrooms, 2 king beds, 2 bathrooms
13–18 Sept
4.87 out of 5 average rating, 15 reviews
Guest favourite
Home in Afton
CritzerHouse - on 151- Walk to the Brewery!
4 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.95 out of 5 average rating, 274 reviews
Top guest favourite
Flat in Afton
The Meadows of White Mountain
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept