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Search results; Over 1,000 homes in Middleburg

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Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 private bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 81 reviews
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Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 113 reviews
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Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Middleburg
Historic Middleburg Equestrian Estate
5 bedrooms, 5 beds, 5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 52 reviews
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Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
22–27 Sept
4.95 out of 5 average rating, 103 reviews
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Guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 131 reviews
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Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 142 reviews
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Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
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Top guest favourite
Flat in Middleburg
Middleburg Carriage House Flat Coachman’s Quarters
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 220 reviews
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Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 223 reviews
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Guest favourite
Home in Middleburg
Salamander/Downtown Middleburg.
3 bedrooms, 2 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 38 reviews
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Guest favourite
Home in Middleburg
Hunt Country Stone Cottage
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.86 out of 5 average rating, 14 reviews
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Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
14–19 Dec
4.94 out of 5 average rating, 240 reviews
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Guest favourite
Home in Aldie
Aldie Home w/ Private Pool: Near Wineries!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Dec
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Leesburg
Historic Schoolhouse Retreat
2 bedrooms, 2 beds, 1 bathroom
22–27 Sept
4.98 out of 5 average rating, 66 reviews
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Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 732 reviews
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Guest favourite
Farm stay in Middleburg
Self-contained apartment on Organic vegetable farm
1 bedroom, 2 beds, 1 bathroom
1–6 Jan
4.92 out of 5 average rating, 166 reviews