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Search results; Over 1,000 homes in Middleburg

Guest favourite
Home in Middleburg
Historic country retreat, a piece of quiet heaven.
2 bedrooms, 2 beds, 2.5 shared bathrooms
1–6 Aug
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5.0 out of 5 average rating, 46 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 74 reviews
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 54 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
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
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
New place to stay
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
18–23 Sept
4.94 out of 5 average rating, 234 reviews
Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 107 reviews
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 126 reviews
Guest favourite
Flat in The Plains
Charming barn apartment in horse /wine country
1 bedroom, 1 double bed, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 86 reviews
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
4.96 out of 5 average rating, 214 reviews
Guest favourite
Home in Middleburg
Salamander/Downtown Middleburg.
3 bedrooms, 2 beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 37 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Farm stay in Purcellville
Country Cottage on 1700’s Quaker Farm
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 215 reviews
Guest favourite
Home in Middleburg
Peaceful, Authentic Stone Cottage with Cozy Charm
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
4.94 out of 5 average rating, 86 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
4.97 out of 5 average rating, 282 reviews