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Search results; Over 1,000 homes in Middleburg

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Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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5.0 out of 5 average rating, 139 reviews
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Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 111 reviews
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Villa in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 26 reviews
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Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 78 reviews
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Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 101 reviews
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Flat in The Plains
Charming barn apartment in horse /wine country
1 bedroom, 1 double bed, 1 bathroom
26 Sept – 1 Oct
4.92 out of 5 average rating, 24 reviews
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Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 129 reviews
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Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
2 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews
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Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
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Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 238 reviews
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Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 58 reviews
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Top guest favourite
Cottage in Middleburg
English Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 154 reviews
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Guest house in Middleburg
Tranquil Country Gem
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 80 reviews
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Room in The Plains
Cherry Blossom Room- 1 full, one twin
2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 24 reviews
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Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 12 reviews
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Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 220 reviews
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Loft in Purcellville
Saddle Tree at Akeley Wood Farm
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 97 reviews
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Home in Middleburg
Hunt Country Stone Cottage
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.85 out of 5 average rating, 13 reviews