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Search results; Over 1,000 homes in Leesburg

Guest favourite
Cottage in Leesburg
The Cottage at Stone Tower Winery
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 299 reviews
Top guest favourite
Home in Leesburg
Downtown Leesburg Cottage. Walk to everything!
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 213 reviews
Top guest favourite
Apartment in Leesburg
Downtown 1 BR Condo Steps to Everything
1 bedroom, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.94 out of 5 average rating, 285 reviews
Top guest favourite
Home in Leesburg
New Leesburg Stay
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Leesburg
Chalet at Stone Tower Winery
4 bedrooms, 5 beds, 3 bathrooms
27 Oct – 1 Nov
4.93 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Leesburg
Historic Leesburg location with so much more!
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 508 reviews
Top guest favourite
Flat in Leesburg
Blue Skies
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Leesburg
Spacious, Luxury Property - Downtown Leesburg
4 bedrooms, 4 beds, 2.5 bathrooms
7–12 Dec
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Ashburn
Ashburn Manor: 1920’s Farmhouse
3 bedrooms, 4 beds, 2 bathrooms
16–21 Oct
4.99 out of 5 average rating, 129 reviews
Guest favourite
Home in Leesburg
The Hound's House at Stable & Vine
2 bedrooms, 2 beds, 2 bathrooms
14–20 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Leesburg
The Garage Mahal w/Hot Tub
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Leesburg
Spring House at Stone Tower Winery
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in Hamilton
Ballenger Farm
4 bedrooms, 6 beds, 3.5 bathrooms
19–24 Sept
4.98 out of 5 average rating, 280 reviews
Guest favourite
Flat in Leesburg
Cosy one bedroom apartment in Leesburg
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Leesburg
Modern Farmhouse Wine Retreat Fire Pit Sunset View
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Paeonian Springs
Cozy Haven Cottage - Wedding and Winery Retreat
2 bedrooms, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Sterling
The Villa on Lakeside
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 144 reviews
Guest favourite
Cottage in Leesburg
Vinegar Hill Cottage in historic downtown Leesburg
3 bedrooms, 4 beds, 2.5 bathrooms
31 Oct – 5 Nov
4.95 out of 5 average rating, 101 reviews
Top guest favourite
Rooms in Leesburg
Max & Boo's house
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews