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Search results; Over 1,000 homes in Middleburg

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Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 private bathroom
25–30 Oct
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4.99 out of 5 average rating, 223 reviews
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Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 81 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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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
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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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
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
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.94 out of 5 average rating, 240 reviews
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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
Guest house in Middleburg
Lovely spacious one-bedroom guest house
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 116 reviews
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Top guest favourite
Farm stay in Middleburg
Retreat to horse country!
1 bedroom, 1 bed, 1.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 104 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
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, 219 reviews
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Cottage in Middleburg
Welcome home to the hummingbird house
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.82 out of 5 average rating, 57 reviews
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Superhost
Home in Middleburg
super cosy cottage with high speed internet
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.85 out of 5 average rating, 316 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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Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
2 bedrooms, 2 single beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 11 reviews