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Search results; Over 1,000 homes in Saint Leonard

Home in St. Leonard
Perfect Bay and Beach Getaway one hour from DC!
5 bedrooms, 6 beds, 4.5 private bathrooms
21–26 Aug
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4.86 out of 5 average rating, 138 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, 7 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
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 94 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
Guest suite in St. Leonard
Exclusive Waterfront Getaway
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 37 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
Guest house in St. Leonard
Studio on the Bay.
1 bedroom, 1 queen bed, 1 bathroom
26–31 Aug
4.97 out of 5 average rating, 124 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, 19 reviews
Home in St. Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
5 bedrooms, 8 beds, 2.5 bathrooms
23–28 Aug
4.69 out of 5 average rating, 133 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, 23 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
Cabin in St. Leonard
Beach Access Cozy Cedar Cottage
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Aug
4.95 out of 5 average rating, 95 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
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, 68 reviews
Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 59 reviews
Rooms in St. Leonard
Chesapeake Historic Circa 1825 Curated Farm Stay
4 bedrooms, 3 queen beds, 2 bathrooms
21–26 Aug
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
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
20–26 Aug
4.92 out of 5 average rating, 37 reviews