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Search results; Over 1,000 homes in Hillsboro

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Top guest favourite
Holiday home in Hillsboro
Farwell Cottage c.1752 New Renovated Historic Home
3 bedrooms, 3 beds, 2.5 private bathrooms
26–31 Oct
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4.99 out of 5 average rating, 106 reviews
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Villa in Hillsboro
Historic Home with Pool in Virginia Wine Country
6 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
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Villa in Purcellville
Amazing Guitar Pool 11200sf Private Oasis hot tub
9 bedrooms, 17 beds
14–19 Sept
4.92 out of 5 average rating, 208 reviews
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Cabin in Harpers Ferry
~Family Friendly Mountain Cabin w/ Steam Shower!
2 bedrooms, 3 beds
7–12 Sept
4.97 out of 5 average rating, 97 reviews
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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
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Cabin in Harpers Ferry
Treetop Mountain Retreat- Almost Heaven
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 71 reviews
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Hotel room in Waterford
Burgundy Room - Loudoun Valley Manor
1 bedroom, 1 king bed
7–12 Sept
5.0 out of 5 average rating, 18 reviews
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Cottage in Purcellville
Historic Stone Schoolhouse on Winery Row
2 bedrooms, 2 beds
11–16 Oct
4.94 out of 5 average rating, 83 reviews
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Bed and breakfast in Waterford
Redwood suite - Loudoun Valley Manor
1 bedroom, 1 king bed
6–11 Sept
5.0 out of 5 average rating, 21 reviews
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Home in Purcellville
Whole House -Seven Elms Farm B&B
3 bedrooms, 5 beds
8–13 Sept
4.99 out of 5 average rating, 344 reviews
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Room in Hamilton
1 Private Bed & bathroom in Our Lovely House
1 queen bed
6–11 Sept
4.96 out of 5 average rating, 70 reviews
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Cottage in Purcellville
Historic Wheatland Log Cabin
1 bedroom, 1 queen bed
17–22 Nov
4.98 out of 5 average rating, 65 reviews
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Home in Purcellville
The Cabin at Blue Valley Farm
1 bedroom, 2 beds
4–9 Oct
4.96 out of 5 average rating, 50 reviews
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Home in Harpers Ferry
Mountaintop Home in Harpers Ferry
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 91 reviews
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Home in Purcellville
The Carriage House— Circa 1937
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 19 reviews
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Farm stay in Hillsboro
Homestead 1870 in Wine Country
2 bedrooms, 2 beds
11–16 Sept
4.95 out of 5 average rating, 218 reviews
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Flat in Harpers Ferry
Mountain Chic Retreat w/ Lake Beach Passes!
2 bedrooms, 4 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 62 reviews
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Home in Purcellville
Artist Retreat
2 bedrooms, 3 beds
14–19 Oct
4.76 out of 5 average rating, 21 reviews
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Home in Bluemont
Touch of Tuscan - Minutes to Wine, Beer, Hiking
3 bedrooms, 4 beds
6–11 Sept
4.9 out of 5 average rating, 31 reviews