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Search results; Over 1,000 homes in Leesburg

Top guest favourite
Apartment in Leesburg
Downtown 1 BR Condo Steps to Everything
1 bedroom, 2 beds, 1 private bathroom
8–13 Nov
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4.94 out of 5 average rating, 287 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, 214 reviews
Guest favourite
Home in Leesburg
The Hound's House at Stable & Vine
2 bedrooms, 2 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Loft in Leesburg
UpperLVL/Loft/Farmhouse sleeps 8/WineCountry
3 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
4.88 out of 5 average rating, 8 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
Home in Leesburg
New Leesburg Stay
3 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Leesburg
Historic Schoolhouse Retreat
2 bedrooms, 2 beds, 1 bathroom
22–27 Sept
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Guest house in Hamilton
Trailside Chalet (A storybook chalet with hot tub)
2 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 183 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
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
Villa in Leesburg
The Garage Mahal w/Hot Tub
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Farm stay in Hamilton
Historic Manor on Beautiful 150 acre Farm
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Leesburg
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Leesburg
Porches and King Beds
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 42 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
Top guest favourite
Home in Leesburg
The Watson Farm House
5 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 67 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
Guest favourite
Home in Leesburg
Oatlands - The Retreat
6 bedrooms, 8 beds, 5.5 bathrooms
15–20 Sept
4.88 out of 5 average rating, 85 reviews
Guest favourite
Guest house in Leesburg
Private 2 King BR, 1 BA Apartment Near Wineries!
2 bedrooms, 2 king beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 119 reviews