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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 Greenwood
Ramsay Estate | Historic Cottage on Vineyard
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 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, 162 reviews
Top guest favourite
Guest house in Crozet
Elegant and Convenient in Crozet
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 582 reviews
Guest favourite
Home in Charlottesville
Pine Lake Lodge
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.93 out of 5 average rating, 243 reviews
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 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
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, 253 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 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
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 Charlottesville
Casa Crozet
3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
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, 351 reviews
Superhost
Home in Crozet
Stockton Creek Farmhouse | 100 Acre Farm Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
Top guest favourite
Home in Afton
The Vū, Afton w/ 360º Mountain Views
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Nov
5.0 out of 5 average rating, 65 reviews
Guest favourite
Cottage in Crozet
High Street | Walk to Everything Crozet | Pet-Frie
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 282 reviews
Top guest favourite
Cottage in Charlottesville
Mechums River Nature Retreat
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 247 reviews
Top guest favourite
Cabin in Afton
Afton Mountain Retreat - The Cabin
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.91 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Greenwood
Private Carriage House, close to Shenandoah & 151
1 bedroom, 1 bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 70 reviews