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Search results; Over 1,000 homes in Saint Leonard

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Top guest favourite
Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
3 bedrooms, 6 beds, 2 shared bathrooms
13–18 Oct
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4.92 out of 5 average rating, 199 reviews
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Guest favourite
Home in St. Leonard
Shewells Cottage at Long Beach
3 bedrooms, 6 beds
26 Sept – 1 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
1–6 Oct
4.94 out of 5 average rating, 199 reviews
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Guest favourite
Flat in St. Leonard
The Loft at Flag Harbor
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.89 out of 5 average rating, 19 reviews
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Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds
15–21 May
4.92 out of 5 average rating, 37 reviews
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Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds
21–26 Sept
4.91 out of 5 average rating, 97 reviews
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Guest favourite
Place to stay in St. Leonard
Mermaids Paradise
1 bedroom, 2 beds
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
11–16 Oct
4.97 out of 5 average rating, 107 reviews
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Home in St. Leonard
Waterfront – Private Beach & Beautiful Water Views
4 bedrooms, 5 beds
20–25 Sept
New place to stay
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Top guest favourite
Home in St. Leonard
Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks
5 bedrooms, 8 beds
20–25 Sept
4.96 out of 5 average rating, 89 reviews
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Cottage in St. Leonard
Spacious Beachfront Retreat w/Dock
5 bedrooms, 9 beds
20–25 Sept
4.82 out of 5 average rating, 145 reviews
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Top guest favourite
Home in St. Leonard
Cottage on the Bay
2 bedrooms, 3 beds
13–18 Oct
4.94 out of 5 average rating, 99 reviews
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Guest favourite
Home in St. Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 bedrooms, 3 double beds
21–26 Sept
4.85 out of 5 average rating, 80 reviews
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Guest favourite
Home in Prince Frederick
Chesapeake Escape Southern Md, Bay Adventures!
3 bedrooms, 7 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 57 reviews
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Home in St. Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
5 bedrooms, 8 beds
3–8 Oct
4.69 out of 5 average rating, 134 reviews
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Guest favourite
Cottage in Port Republic
Shewell’s Cottage by the Shore
3 bedrooms, 4 beds
20–25 Sept
4.8 out of 5 average rating, 220 reviews
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Flat in St. Leonard
Highland Cow Apartment in St Leonard
1 bedroom, 1 king bed
25–30 Sept
New place to stay
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Top guest favourite
Home in St. Leonard
Closest Home to Private Beach • Stunning Bay Views
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds
20–25 Sept
4.96 out of 5 average rating, 24 reviews