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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
23–28 Aug
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5.0 out of 5 average rating, 238 reviews
Superhost
Home in Crozet
Cottage on Working Farm near Vineyards
4.68 out of 5 average rating, 53 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
Guest favourite
Cabin in Waynesboro
Vintage Log Cabin close to wineries & hiking
4.93 out of 5 average rating, 85 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Farm stay in Afton
Afton, Mountain View Mini Farm
4.99 out of 5 average rating, 342 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Cottage in Crozet
The Carriage House
4.9 out of 5 average rating, 287 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Guest favourite
Cottage in Afton
GreenHouseNelson
4.87 out of 5 average rating, 511 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Home in Charlottesville
40 Acre - Mechum Hill - Main House - Farm Stay
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Guest favourite
Cottage in Charlottesville
The Ivy Rose Tea House, 15 min to Cville & Mtns
4.93 out of 5 average rating, 151 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest suite in Crozet
Guesthouse at Hamilton Oaks
4.98 out of 5 average rating, 246 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
4.96 out of 5 average rating, 270 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Afton
Rockwell Ridge | Garden Suite with Full Kitchen
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Greenwood
Ramsay Estate | Historic Cottage on Vineyard
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Home in Afton
26 Acres/Mtn Views/Hot Tub/Firepit/Privacy!
4.97 out of 5 average rating, 70 reviews, 4 bedrooms, 6 beds, 3 bathrooms
20–25 Aug
Top guest favourite
Home in Waynesboro
Scenic Blue Ridge Sanctuary
4.93 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Chalet in Afton
Elk Mountain Overlook: Breathtaking Views
4.99 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
Guest favourite
Home in Waynesboro
Prickly Pear Cottage *5 minutes from skyline dr.*
4.84 out of 5 average rating, 203 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Cottage in Afton
The Cottage @ Afton Mountain- Close to Wineries!
4.98 out of 5 average rating, 298 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Charlottesville
Mechums River Nature Retreat
4.97 out of 5 average rating, 243 reviews, 2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
Top guest favourite
Guest house in Waynesboro
The Stable
4.92 out of 5 average rating, 481 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept