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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
18–23 Oct
5.0 out of 5 average rating, 213 reviews
Top guest favourite
Rooms in Leesburg
Max & Boo's house
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews
Guest favourite
Home in Leesburg
The Hound's House at Stable & Vine
2 bedrooms, 2 beds
14–20 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Leesburg
Downtown 1 BR Condo Steps to Everything
1 bedroom, 2 beds
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
13–18 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Leesburg
Historic Leesburg location with so much more!
1 bedroom, 1 queen bed
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
19–24 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Leesburg
Blue Skies
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Guest house in Leesburg
CozyLeesburgCottage-Private Home Downtown Leesburg
1 bedroom, 1 queen bed
16–21 Nov
4.96 out of 5 average rating, 584 reviews
Guest favourite
Guest house in Leesburg
Private 2 King BR, 1 BA Apartment Near Wineries!
2 bedrooms, 2 king beds
18–23 Sept
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Leesburg
Porches and King Beds
2 bedrooms, 2 king beds
20–25 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Treehouse in Leesburg
Romantic Secluded Treehouse Stay in the Sky
1 bedroom, 2 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 478 reviews
Top guest favourite
Guest house in Hamilton
Trailside Chalet (A storybook chalet with hot tub)
2 bedrooms, 5 beds
13–18 Sept
4.96 out of 5 average rating, 183 reviews
Top guest favourite
Home in Leesburg
Spacious, Luxury Property - Downtown Leesburg
4 bedrooms, 4 beds
7–12 Dec
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Guest house in Leesburg
Downtown Private Guesthouse - Cozy Bungalow
2 bedrooms, 2 beds
8–13 Dec
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Leesburg
The Quarters at Belgrove
2 bedrooms, 2 beds
11–16 Oct
5.0 out of 5 average rating, 226 reviews
Guest favourite
Loft in Leesburg
UpperLVL/Loft/Farmhouse sleeps 8/WineCountry
3 bedrooms, 6 beds
13–18 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Hamilton
Historic Manor on Beautiful 150 acre Farm
3 bedrooms, 4 beds
13–18 Sept
4.97 out of 5 average rating, 75 reviews