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Search results; Over 1,000 homes in Greenwood

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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, 70 reviews
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Home in Afton
The Cupola Creek House
4 bedrooms, 8 beds, 3 bathrooms
7–12 Sept
New place to stay
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Guest house in Crozet
Birds & Bees Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Dec
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Home in Waynesboro
Cute Place in Waynesboro
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 68 reviews
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Home in Charlottesville
Casa Crozet
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.98 out of 5 average rating, 40 reviews
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Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
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Home in Charlottesville
6-Acre Escape Near UVA & Wineries! King Suite
4 bedrooms, 9 beds, 3.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 88 reviews
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Home in Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.93 out of 5 average rating, 242 reviews
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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, 71 reviews
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Cottage in Afton
The Wine Cottage | 5BR w/ Hot Tub Near Nelson 151
5 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 78 reviews
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Guest suite in Crozet
Guesthouse at Hamilton Oaks
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 249 reviews
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Home in Crozet
Carter Street | Walkable Crozet | Pet-Friendly
3 bedrooms, 3 queen beds, 2 bathrooms
8–13 Sept
4.88 out of 5 average rating, 17 reviews
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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, 304 reviews
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Farm stay in Afton
Afton, Mountain View Mini Farm
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 350 reviews
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Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 9 reviews
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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, 220 reviews
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Cottage in Afton
The Little Farmhouse | Hot Tub & Wine Country
3 bedrooms, 3 king beds, 2 bathrooms
4–9 Sept
4.97 out of 5 average rating, 71 reviews
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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, 241 reviews
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Home in Afton
Wine Country Retreat Near National Park
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 32 reviews