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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, 239 reviews
Top guest favourite
Holiday home in Lovingston
Ultimate cabin in the mountains
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 272 reviews
Top guest favourite
Loft in Afton
One bedroom apartment totally renovated
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 56 reviews
Guest favourite
Cabin in Afton
Afton Mountain Retreat - The Cabin
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.91 out of 5 average rating, 77 reviews
Superhost
Home in Crozet
Blairbrook Farm | Spacious Retreat Near Vineyards
4 bedrooms, 7 beds, 2 bathrooms
10–15 Aug
Guest favourite
Cottage in Crozet
The Carriage House
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.89 out of 5 average rating, 288 reviews
Guest favourite
Home in Afton
The Branch at Afton Mountain Retreat
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Cabin in Free Union
Shenandoah Stargazer with Sauna
3 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 237 reviews
Guest favourite
Cottage in Charlottesville
Pounding Creek Cottage
2 bedrooms, 3 beds, 2 bathrooms
14–19 Aug
4.86 out of 5 average rating, 136 reviews
Top guest favourite
Home in Afton
The Goldfinch
2 bedrooms, 2 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Charlottesville
The Peony Cottage in Charlottesville
2 bedrooms, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 102 reviews
Superhost
Cottage in Crozet
Idyllic Cottage Retreat
2 bedrooms, 1 bathroom
1–6 Dec
4.89 out of 5 average rating, 257 reviews
Top guest favourite
Tiny home in Faber
The Stilt House at Perkins Hollow
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Waynesboro
Prickly Pear Cottage *5 minutes from skyline dr.*
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.84 out of 5 average rating, 204 reviews
Top guest favourite
Home in Afton
Glass Hollow Get-away
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Nellysford
Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Home in Afton
Rockwell Ridge | Garden Suite with Full Kitchen
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cabin in Waynesboro
Vintage Log Cabin close to wineries & hiking
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 86 reviews
Guest favourite
Cottage in Charlottesville
The Ivy Rose Tea House, 15 min to Cville & Mtns
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Aug
4.93 out of 5 average rating, 153 reviews