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Search results; Over 1,000 homes in Saint Leonard

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Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 private bathroom
1–6 Oct
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4.91 out of 5 average rating, 97 reviews
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Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
15–21 May
4.92 out of 5 average rating, 37 reviews
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Guest favourite
Home in St. Leonard
Shewells Cottage at Long Beach
3 bedrooms, 6 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Cottage in St. Leonard
Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC
2 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 200 reviews
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Guest favourite
Flat in St. Leonard
The Loft at Flag Harbor
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.89 out of 5 average rating, 19 reviews
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Top guest favourite
Home in St. Leonard
Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks
5 bedrooms, 8 beds, 3.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 89 reviews
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Home in St. Leonard
Waterfront – Private Beach & Beautiful Water Views
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
3 bedrooms, 6 beds, 2 bathrooms
13–18 Oct
4.92 out of 5 average rating, 199 reviews
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Top guest favourite
Home in St. Leonard
Cottage on the Bay
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.94 out of 5 average rating, 99 reviews
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Guest favourite
Place to stay in St. Leonard
Mermaids Paradise
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.93 out of 5 average rating, 201 reviews
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Top guest favourite
Home in St. Leonard
Blue Pearl-Luxury estate with private dock/jacuzzi
4 bedrooms, 4 beds, 3 bathrooms
11–16 Oct
4.97 out of 5 average rating, 107 reviews
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Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 24 reviews
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Guest favourite
Cottage in Port Republic
Shewell’s Cottage by the Shore
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.8 out of 5 average rating, 220 reviews
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Guest favourite
Cabin in St. Leonard
Beach Access Cozy Cedar Cottage
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 96 reviews
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Guest favourite
Home in St. Leonard
The Bay House at Long Beach
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 22 reviews
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Flat in St. Leonard
Highland Cow Apartment in St Leonard
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
New place to stay
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Cottage in St. Leonard
Spacious Beachfront Retreat w/Dock
5 bedrooms, 9 beds, 3 bathrooms
3–8 Oct
4.82 out of 5 average rating, 145 reviews
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Guest favourite
Home in Prince Frederick
Chesapeake Escape Southern Md, Bay Adventures!
3 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 58 reviews
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Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 59 reviews