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Search results; Over 1,000 homes in Middleburg

Top guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 private bathrooms
15–20 Aug
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4.96 out of 5 average rating, 215 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 77 reviews
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds
21–26 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed
22–27 Aug
5.0 out of 5 average rating, 135 reviews
Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed
18–23 Aug
4.98 out of 5 average rating, 109 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 57 reviews
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds
22–27 Aug
4.95 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Flat Coachman’s Quarters
2 bedrooms, 2 beds
16–21 Aug
5.0 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds
2–7 Nov
4.95 out of 5 average rating, 237 reviews
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 queen bed
23–28 Aug
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Farm stay in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds
18–23 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Studio - The Loft
1 bedroom, 1 queen bed
16–21 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds
15–20 Nov
4.95 out of 5 average rating, 314 reviews
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
2 bedrooms, 2 single beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 218 reviews
Top guest favourite
Home in Middleburg
Historic Middleburg Equestrian Estate
5 bedrooms, 5 beds
5–10 Sept
4.96 out of 5 average rating, 48 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Farm stay in Middleburg
Gorgeous historic stone house with great internet!
3 bedrooms, 3 beds
28 Aug – 2 Sept
4.95 out of 5 average rating, 57 reviews
Guest favourite
Flat in The Plains
Charming barn apartment in horse /wine country
1 bedroom, 1 double bed
23–28 Aug
4.92 out of 5 average rating, 24 reviews