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Search results; Over 1,000 homes in Greenwood

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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
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Top guest favourite
Guest house in Greenwood
Private Carriage House, close to Shenandoah & 151
1 bedroom, 1 bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 75 reviews
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Guest favourite
Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Superhost
Tiny home in Afton
Luxury Treehouse • 151 Brew/WineTrail • King Bed
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
New place to stay
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Superhost
Home in Crozet
Cottage on Working Farm near Vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.68 out of 5 average rating, 53 reviews
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Superhost
Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
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Top guest favourite
Guest suite in Crozet
Guesthouse at Hamilton Oaks
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 252 reviews
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Top guest favourite
Home in Afton
Fall Retreat in Wine Country & Near National Park
3 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Greenwood
Ramsay Estate | Carriage House w/ Mountain Views
1 bedroom, 1 king bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 34 reviews
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Home in Charlottesville
Fab Modern Barn w/pool, near UVA
5 bedrooms, 5 beds, 3.5 bathrooms
1–6 Jan
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Top guest favourite
Bungalow in Afton
The Bungalow at Afton Mountain Retreat by Veritas
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
4.99 out of 5 average rating, 254 reviews
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Guest favourite
Home in Afton
Farmhouse on Working Vineyard
5 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
4.94 out of 5 average rating, 163 reviews
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Top guest favourite
Home in Afton
The Inn at Blue Mountain Brewery
5 bedrooms, 8 beds, 3.5 bathrooms
1–6 Nov
4.98 out of 5 average rating, 179 reviews
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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, 127 reviews
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Top guest favourite
Flat in Afton
Mountain View Getaway
1 bed, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 208 reviews
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Guest favourite
Cottage in Afton
Monticello Wine Trail Cottage - Close to Hiking!
2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Guest suite in Waynesboro
The LoriAnn, A Boutique Stay New Sleep Number Bed
1 bedroom, 1 king bed, 1 bathroom
7–12 Nov
4.99 out of 5 average rating, 441 reviews
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Guest favourite
Home in Charlottesville
Casa Crozet
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 43 reviews
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Top guest favourite
Guest house in Crozet
Crozet Cottage | Close to Wineries & DT Crozet
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 236 reviews