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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
9–14 Aug
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4.99 out of 5 average rating, 217 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
5.0 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Barn in Middleburg
The Hayloft
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
5.0 out of 5 average rating, 7 reviews, 9 bedrooms, 9 beds, 5.5 bathrooms
6–11 Sept
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
4.96 out of 5 average rating, 99 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
5.0 out of 5 average rating, 132 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
4.96 out of 5 average rating, 127 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Barn in Middleburg
The Studio
4.98 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
4.96 out of 5 average rating, 214 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Guest favourite
Home in Middleburg
Peaceful, Authentic Stone Cottage with Cozy Charm
4.94 out of 5 average rating, 86 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
4.94 out of 5 average rating, 234 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Sept
Home in Upperville
Virginia Horse and Wine Country Farm Stay
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Guest favourite
Barn in Middleburg
Middleburg Carriage House
4.93 out of 5 average rating, 228 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Farm stay in Purcellville
Country Cottage on 1700’s Quaker Farm
4.98 out of 5 average rating, 171 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Farm stay in Middleburg
Retreat to horse country!
4.97 out of 5 average rating, 100 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
9–14 Aug
Top guest favourite
Home in Middleburg
Middleburg country home
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug