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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 Afton
Farmhouse on Working Vineyard
5 bedrooms, 6 beds, 3 bathrooms
10–15 Sept
4.94 out of 5 average rating, 163 reviews
Guest favourite
Home in Waynesboro
Prickly Pear Cottage *5 minutes from skyline dr.*
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 209 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
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
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 Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.93 out of 5 average rating, 243 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 Waynesboro
Scenic Blue Ridge Sanctuary
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 254 reviews
Top guest favourite
Guest suite in Crozet
Guesthouse at Hamilton Oaks
1 bedroom, 2 beds, 1 bathroom
10–15 Nov
4.98 out of 5 average rating, 251 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
Home in Charlottesville
Modern Farmhouse w/POOL. Work Retreat.
3 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.9 out of 5 average rating, 10 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
Top guest favourite
Home in Charlottesville
40 Acre - Mechum Hill - Main House - Farm Stay
4 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 12 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
Home in Afton
The Cupola Creek House
4 bedrooms, 8 beds, 3 bathrooms
12–17 Sept
New place to stay
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
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, 584 reviews