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Search results; Over 1,000 homes in Round Hill

Guest favourite
Cottage in Round Hill
Private 24-Acre Countryside Retreat - No Fees!
3 bedrooms, 5 beds, 1 private bathroom
29 Aug – 3 Sept
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4.92 out of 5 average rating, 225 reviews
Home in Round Hill
Location, Location, Location in Round Hill, VA
3 bedrooms, 4 beds
21–26 Aug
4.97 out of 5 average rating, 87 reviews
Guest favourite
Cabin in Round Hill
Cozy Creekside Cabin with Great Room/Hot Tub
6 bedrooms, 8 beds
28 Aug – 2 Sept
4.87 out of 5 average rating, 71 reviews
Top guest favourite
Cottage in Round Hill
Farm winery cottage with mountain & vineyard views
2 bedrooms, 2 queen beds
26–31 Aug
4.99 out of 5 average rating, 86 reviews
Guest favourite
Home in Round Hill
New! Blue Ridge Oasis
5 bedrooms, 5 beds
16–21 Nov
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Guest house in Round Hill
Wine Country Loft
1 bedroom, 2 beds
23–28 Aug
4.94 out of 5 average rating, 70 reviews
Cabin in Bolivar
Black Bear Retreat • Modern Cabin in the Woods
2 bedrooms, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Bluemont
Touch of Tuscan - Minutes to Wine, Beer, Hiking
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Harpers Ferry
Gaming Gazebo, Hot Tub, Sauna, Cold Plunge & Golf
3 bedrooms, 4 beds
16–21 Oct
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Round Hill
Countryside Cottage
2 bedrooms, 3 beds
20–25 Aug
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Round Hill
Wine Country Retreat | Hot Tub + Mountain Views
5 bedrooms, 6 beds
21–26 Aug
4.94 out of 5 average rating, 90 reviews
Top guest favourite
Farm stay in Purcellville
Cozy Cuddle up on 1700’s Clydesdale Farm
1 bedroom, 1 queen bed
25–30 Aug
4.99 out of 5 average rating, 394 reviews
Top guest favourite
Home in Round Hill
Historic Farmhouse, Fully Renovated in Fall 2023
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 89 reviews
Guest favourite
Farm stay in Round Hill
Little Round Top Farm - A country getaway!
1 bedroom, 1 bed
23–28 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds
30 Nov – 5 Dec
4.97 out of 5 average rating, 128 reviews
Cabin in Round Hill
Hilltop Retreat
4 bedrooms, 5 beds
21–26 Aug
4.78 out of 5 average rating, 36 reviews
Guest favourite
Home in Bluemont
Beautiful Cottage in the Heart of Wine Country
2 bedrooms, 3 beds
19–24 Aug
4.9 out of 5 average rating, 120 reviews
Guest favourite
Guest house in Purcellville
The Carriage House: Pathway to a Romantic Getaway
1 bed
6–11 Sept
4.97 out of 5 average rating, 134 reviews
Top guest favourite
Flat in Purcellville
Starry Night Apt in Va Wine Country
1 bedroom, 2 beds
25–30 Aug
4.98 out of 5 average rating, 107 reviews