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Search results; Over 1,000 homes in Saint Leonard

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Guest favourite
Flat in St. Leonard
The Loft at Flag Harbor
2 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.89 out of 5 average rating, 19 reviews
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Guest favourite
Home in St. Leonard
Shewells Cottage at Long Beach
3 bedrooms, 6 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 9 reviews
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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, 196 reviews
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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, 105 reviews
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Guest favourite
Home in St. Leonard
Hickory House on the Chesapeake Bay!
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.93 out of 5 average rating, 96 reviews
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Guest favourite
Home in St. Leonard
Block to beach! Relax, enjoy views & game room.
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.94 out of 5 average rating, 69 reviews
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Home in St. Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
5 bedrooms, 8 beds, 2.5 bathrooms
1–6 Sept
4.69 out of 5 average rating, 133 reviews
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Guest favourite
Home in St. Leonard
Escape to the Bay~Waterfront
4 bedrooms, 6 beds, 4 bathrooms
2–8 Sept
4.92 out of 5 average rating, 37 reviews
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Top guest favourite
Home in St. Leonard
Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks
5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 88 reviews
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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, 98 reviews
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Guest favourite
Home in St. Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 bedrooms, 3 double beds, 1 bathroom
8–13 Sept
4.86 out of 5 average rating, 79 reviews
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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
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Guest favourite
Home in St. Leonard
Waterfront Home, Spectacular View & Private Beach!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 23 reviews
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Home in St. Leonard
Perfect Bay and Beach Getaway one hour from DC!
5 bedrooms, 6 beds, 4.5 bathrooms
29 Sept – 4 Oct
4.86 out of 5 average rating, 139 reviews
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Guest favourite
Home in St. Leonard
Cozy Beach Retreat (Pets Allowed) 3 Queen Beds
3 bedrooms, 3 queen beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 8 reviews
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Cottage in St. Leonard
Spacious Beachfront Retreat w/Dock
5 bedrooms, 9 beds, 3 bathrooms
13–18 Sept
4.83 out of 5 average rating, 142 reviews
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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, 24 reviews
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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, 39 reviews
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Guest favourite
Home in St. Leonard
OLD BAY beach-front classic on the Chesapeake Bay
3 bedrooms, 3 king beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 59 reviews