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Search results; Over 1,000 homes in Saint Leonard

Guest favourite
Home in St. Leonard
Block to beach! Relax, enjoy views & game room.
3 bedrooms, 5 beds, 2.5 private bathrooms
23–28 Aug
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4.96 out of 5 average rating, 68 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, 6 reviews
Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 94 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
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
Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
17–23 Aug
4.92 out of 5 average rating, 37 reviews
Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
4.95 out of 5 average rating, 21 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, 77 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
Guest favourite
Guest suite in St. Leonard
Exclusive Waterfront Getaway
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 36 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, 21 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, 26 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, 103 reviews
Cottage in St. Leonard
Spacious Beachfront Retreat w/Dock
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
4.84 out of 5 average rating, 141 reviews
Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
20–25 Aug
5.0 out of 5 average rating, 59 reviews
Guest favourite
Cabin in St. Leonard
Beach Access Cozy Cedar Cottage
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Aug
4.95 out of 5 average rating, 95 reviews
Guest favourite
Cottage in Port Republic
Shewell’s Cottage by the Shore
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.79 out of 5 average rating, 219 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