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Search results; Over 1,000 homes in Saint Leonard

Top guest favourite
Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
3 bedrooms, 6 beds, 2 shared bathrooms
23–28 Sept
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4.92 out of 5 average rating, 199 reviews
Top guest favourite
Cottage in St. Leonard
Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
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
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 96 reviews
Top guest favourite
Home in St. Leonard
Cottage on the Bay
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 99 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
Top guest favourite
Guest suite in St. Leonard
Exclusive Waterfront Hideaway in St. Leonard
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Lusby
Historic Manor - Main House
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
4.96 out of 5 average rating, 24 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
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
Guest favourite
Home in St. Leonard
Large home w/ 6 Bedrooms, 7 Bathrooms, & Game Room
6 bedrooms, 9 beds, 7 bathrooms
11–16 Sept
4.93 out of 5 average rating, 109 reviews
Top guest favourite
Guest house in St. Leonard
Studio on the Bay.
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 126 reviews
Guest favourite
Home in St. Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 bedrooms, 3 double beds, 1 bathroom
18–23 Oct
4.86 out of 5 average rating, 79 reviews
Top guest favourite
Home in St. Leonard
Closest Home to Private Beach • Stunning Bay Views
3 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 26 reviews
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
Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
10–16 Sept
4.92 out of 5 average rating, 37 reviews
Rooms in St. Leonard
Chesapeake Historic Circa 1825 Curated Farm Stay
4 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews