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Search results; Over 1,000 homes in Middleburg

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Top guest favourite
Home in Middleburg
Middleburg area overlooking Shenandoah River!
4 bedrooms, 5 beds, 4 private bathrooms
1–6 Oct
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4.98 out of 5 average rating, 57 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 Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 81 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, 64 reviews
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Top guest favourite
Home in Middleburg
Historic Middleburg Equestrian Estate
5 bedrooms, 5 beds, 5 bathrooms
3–8 Oct
4.96 out of 5 average rating, 53 reviews
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Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 114 reviews
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Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
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
26–31 Oct
4.95 out of 5 average rating, 132 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, 143 reviews
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Top guest favourite
Villa in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds, 4.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 220 reviews
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Guest favourite
Home in Middleburg
Hunt Country Stone Cottage
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.87 out of 5 average rating, 15 reviews
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Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Farm stay in Middleburg
Gorgeous historic stone house with great internet!
3 bedrooms, 3 beds, 2.5 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 58 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
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
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Top guest favourite
Farm stay in Middleburg
Retreat to horse country!
1 bedroom, 1 bed, 1.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 105 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, 224 reviews
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Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.97 out of 5 average rating, 287 reviews