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Search results; Over 1,000 homes in Middleburg

Top guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 private bathrooms
20–25 Sept
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4.96 out of 5 average rating, 218 reviews
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, 80 reviews
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
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 Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 62 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, 240 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
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
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
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
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, 81 reviews
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Cottage in Middleburg
English Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 155 reviews
Top guest favourite
Guest suite in The Plains
Luxury hunt country getaway!
1 bedroom, 1 king bed, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 287 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Flat Coachman’s Quarters
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.99 out of 5 average rating, 222 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, 51 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