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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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Guest favourite
Home in Greenwood
Ramsay Estate | Carriage House w/ Mountain Views
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 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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Superhost
Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
28 Sept – 3 Oct
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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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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, 73 reviews
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Guest favourite
Bungalow in Waynesboro
Cheerful 2 bd bungalow with HOT TUB! Pet friendly!
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.93 out of 5 average rating, 409 reviews
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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, 586 reviews
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Guest favourite
Cottage in Afton
Monticello Wine Trail Cottage - Close to Hiking!
2 beds, 1 bathroom
21–26 Sept
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
20–25 Sept
4.99 out of 5 average rating, 439 reviews
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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
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Guest favourite
Home in Afton
Farmhouse on Working Vineyard
5 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.94 out of 5 average rating, 163 reviews
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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
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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
Home in Afton
The Inn at Blue Mountain Brewery
5 bedrooms, 8 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Afton
Mountain Overlook House - Blue Ridge Parkway
2 bedrooms, 2 beds, 2 bathrooms
8–13 Nov
4.99 out of 5 average rating, 110 reviews
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Guest favourite
Home in Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.93 out of 5 average rating, 243 reviews
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Home in Afton
Fall Retreat in Wine Country & Near National Park
3 bedrooms, 5 beds, 2 bathrooms
28 Oct – 2 Nov
4.97 out of 5 average rating, 34 reviews