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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 private bathrooms
20–25 Sept
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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
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
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, 102 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
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
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
Guest favourite
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, 25 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
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
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 7 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, 222 reviews
Top guest favourite
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
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
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
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
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
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
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