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Search results; Over 1,000 homes in Middleburg

Top guest favourite
Cottage in Middleburg
English Cottage
1 bedroom, 2 beds, 1 private bathroom
18–23 Jul
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4.93 out of 5 average rating, 151 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
5.0 out of 5 average rating, 73 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
Top guest favourite
Home in Middleburg
English Cottage/Main House
5.0 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
5.0 out of 5 average rating, 131 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
5.0 out of 5 average rating, 7 reviews, 9 bedrooms, 9 beds, 5.5 bathrooms
19–24 Jul
Top guest favourite
Barn in Middleburg
The Studio
4.98 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
4.96 out of 5 average rating, 98 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
4.96 out of 5 average rating, 214 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
4.94 out of 5 average rating, 233 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
4.96 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
5.0 out of 5 average rating, 85 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Home in Middleburg
Littlefield Cottage
4.99 out of 5 average rating, 215 reviews, 3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
Top guest favourite
Cabin in Marshall
The Serenity Cabin | Firepit | Wineries | Hiking
4.96 out of 5 average rating, 68 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
20–25 Jul
Guest favourite
Farm stay in Middleburg
Gorgeous historic stone house with great internet!
4.95 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
Guest favourite
Home in Middleburg
Peaceful, Authentic Stone Cottage with Cozy Charm
4.94 out of 5 average rating, 86 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Farm stay in Middleburg
Retreat to horse country!
4.97 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Studio - The Loft
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Home in Middleburg
super cosy cottage with high speed internet
4.85 out of 5 average rating, 311 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul