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Search results; Over 1,000 homes in Middleburg

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, 79 reviews
Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 111 reviews
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 7 reviews
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
Top guest favourite
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, 133 reviews
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, 59 reviews
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 239 reviews
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, 102 reviews
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, 27 reviews
Guest favourite
Home in Middleburg
Salamander/Downtown Middleburg.
3 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 37 reviews
Guest favourite
Guest house in Middleburg
Tranquil Country Gem
2 bedrooms, 2 beds, 1 bathroom
1–6 Dec
4.98 out of 5 average rating, 80 reviews
Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Middleburg
Countryside cottage quiet setting in Middleburg
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.97 out of 5 average rating, 76 reviews
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, 50 reviews
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
Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 221 reviews
Top guest favourite
Home in Middleburg
Middleburg country home
4 bedrooms, 6 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 31 reviews
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, 141 reviews