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Search results; Over 1,000 homes in Middleburg

Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 private bathroom
26–31 Jul
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4.99 out of 5 average rating, 215 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 73 reviews
Home in Sperryville
Sommerhus @ Skyline Drive • Modern Scandi Cabin
2 bedrooms, 2 beds, 2.5 bathrooms
30 Jul – 4 Aug
New place to stay
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 132 reviews
Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 107 reviews
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 126 reviews
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
4.96 out of 5 average rating, 214 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 706 reviews
Top guest favourite
Cabin in Front Royal
Mountaintop Retreat with Wood Fired Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 439 reviews
Guest favourite
Flat in The Plains
Charming barn apartment in horse /wine country
1 bedroom, 1 double bed, 1 bathroom
22–27 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Flat Coachman’s Quarters
2 bedrooms, 2 beds, 1 bathroom
22–27 Jul
5.0 out of 5 average rating, 84 reviews
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
2 bedrooms, 2 single beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Farm stay in Purcellville
Country Cottage on 1700’s Quaker Farm
3 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Home in Delaplane
Cobbler Mountain Revival | Historic Farmhouse+View
3 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Guest suite in The Plains
Luxury hunt country getaway!
1 bedroom, 1 king bed, 1 bathroom
28 Jul – 2 Aug
5.0 out of 5 average rating, 168 reviews