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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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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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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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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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Guest house in Crozet
Blue Ridge Retreat
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
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Top guest favourite
Flat in Crozet
Mtn Vineyards Getaway
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 53 reviews
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Guest favourite
Cabin in Afton
Afton Mountain Retreat - The Cabin
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.91 out of 5 average rating, 82 reviews
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Guest favourite
Cabin in Waynesboro
Vintage Log Cabin close to wineries & hiking
3 bedrooms, 3 queen beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 87 reviews
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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, 73 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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Guest favourite
Home in Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
11–16 Oct
4.93 out of 5 average rating, 245 reviews
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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, 251 reviews
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Home in Waynesboro
Basic City Rancher
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 3 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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Superhost
Chalet in Afton
Chalet house next to wineries/breweries!
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.82 out of 5 average rating, 553 reviews
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Guest favourite
Home in Afton
The Branch at Afton Mountain Retreat
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 132 reviews