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Search results; Over 1,000 homes in Saint Leonard

Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 private bathroom
16–21 Aug
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4.93 out of 5 average rating, 94 reviews
Top guest favourite
Cottage in St. Leonard
Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC
2 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 196 reviews
Guest favourite
Home in St. Leonard
Shewells Cottage at Long Beach
3 bedrooms, 6 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Home in St. Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
5 bedrooms, 8 beds, 2.5 bathrooms
16–21 Aug
4.72 out of 5 average rating, 131 reviews
Guest favourite
Flat in St. Leonard
The Loft at Flag Harbor
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
14–20 Aug
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
31 Aug – 5 Sept
4.94 out of 5 average rating, 97 reviews
Top guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in St. Leonard
Exclusive Waterfront Getaway
1 bedroom, 3 beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in St. Leonard
Block to beach! Relax, enjoy views & game room.
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Home in St. Leonard
Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks
5 bedrooms, 8 beds, 3.5 bathrooms
23–28 Aug
4.95 out of 5 average rating, 87 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, 20 reviews
Guest favourite
Home in St. Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 bedrooms, 3 double beds, 1 bathroom
7–12 Sept
4.86 out of 5 average rating, 76 reviews
Guest favourite
Home in St. Leonard
Waterfront! The River's Roost on the Patuxent!
3 bedrooms, 3.5 bathrooms
24–29 Aug
4.88 out of 5 average rating, 25 reviews
Rooms in St. Leonard
Chesapeake Historic Circa 1825 Curated Farm Stay
4 bedrooms, 3 queen beds, 2 bathrooms
15–20 Aug
Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
17–22 Aug
5.0 out of 5 average rating, 59 reviews
Home in St. Leonard
Waterfront house with private beach and pier
4 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
4.78 out of 5 average rating, 65 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, 102 reviews
Guest favourite
Cottage in Port Republic
Shewell’s Cottage by the Shore
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.79 out of 5 average rating, 216 reviews