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Search results; Over 1,000 homes in Middleburg

Guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
1 bedroom, 1 bed, 1 shared bathroom
20–25 Sept
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4.95 out of 5 average rating, 130 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, 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
Top guest favourite
Home in Middleburg
Littlefield Cottage
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 220 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
4–9 Sept
5.0 out of 5 average rating, 7 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, 140 reviews
Guest favourite
Home in Middleburg
Salamander/Downtown Middleburg.
3 bedrooms, 2 beds, 2.5 bathrooms
6–11 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
5–10 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.97 out of 5 average rating, 284 reviews
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, 217 reviews
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
Top guest favourite
Villa in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds, 4.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 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, 91 reviews
Guest favourite
Farm stay in Middleburg
Gorgeous historic stone house with great internet!
3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Cottage in The Plains
Hunt Country Cottage
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 109 reviews
Top guest favourite
Home in Middleburg
Peaceful, Authentic Stone Cottage with Cozy Charm
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.94 out of 5 average rating, 89 reviews
Top guest favourite
Guest house in Middleburg
Lovely spacious one-bedroom guest house
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 115 reviews
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, 9 reviews