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Search results; Over 1,000 homes in Leesburg

Top guest favourite
Farm stay in Leesburg
The Forge on Sunnyside Farm
1 bedroom, 2 beds, 1 private bathroom
13–18 Sept
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5.0 out of 5 average rating, 146 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
Guest favourite
Home in Leesburg
The Hound's House at Stable & Vine
2 bedrooms, 2 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Guest house in Hamilton
Trailside Chalet (A storybook chalet with hot tub)
2 bedrooms, 5 beds, 1 bathroom
9–14 Sept
4.96 out of 5 average rating, 183 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
Red Watson Mountain House
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 139 reviews
Top guest favourite
Farm stay in Hamilton
Historic Manor on Beautiful 150 acre Farm
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 74 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
Top guest favourite
Home in Leesburg
Historic Schoolhouse Retreat
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.98 out of 5 average rating, 66 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
Guest favourite
Loft in Leesburg
UpperLVL/Loft/Farmhouse sleeps 8/WineCountry
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 8 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
The Watson Farm House
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 67 reviews
Top guest favourite
Flat in Leesburg
The Quarters at Belgrove
2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 226 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
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 Leesburg
Hill House
3 bedrooms, 3 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 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