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Search results; Over 1,000 homes in Saint Leonard

Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 beds, 3 private bathrooms
16–21 Sept
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5.0 out of 5 average rating, 59 reviews
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, 198 reviews
Guest favourite
Home in St. Leonard
Shewells Cottage at Long Beach
3 bedrooms, 6 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in St. Leonard
The Loft at Flag Harbor
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Home in St. Leonard
Blue Pearl-Luxury estate with private dock/jacuzzi
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 106 reviews
Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 96 reviews
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
Flat in St. Leonard
Highland Cow Apartment in St Leonard
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
New place to stay
Top guest favourite
Home in St. Leonard
Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks
5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 89 reviews
Cottage in St. Leonard
Spacious Beachfront Retreat w/Dock
5 bedrooms, 9 beds, 3 bathrooms
13–18 Sept
4.82 out of 5 average rating, 145 reviews
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
Top guest favourite
Home in St. Leonard
Cottage on the Bay
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 99 reviews
Top guest favourite
Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
3 bedrooms, 6 beds, 2 bathrooms
23–28 Sept
4.92 out of 5 average rating, 199 reviews
Guest favourite
Home in St. Leonard
The Bay House at Long Beach
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in St. Leonard
Closest Home to Private Beach • Stunning Bay Views
3 bedrooms, 4 beds, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in St. Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 bedrooms, 3 double beds, 1 bathroom
21–26 Sept
4.86 out of 5 average rating, 79 reviews
Home in St. Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
5 bedrooms, 8 beds, 2.5 bathrooms
18–23 Sept
4.69 out of 5 average rating, 134 reviews
Guest favourite
Home in Prince Frederick
Chesapeake Escape Southern Md. Bay Adventures!
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 54 reviews