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Search results; Over 1,000 homes in Saint Leonard

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Guest favourite

Home in St. Leonard

Block to beach! Relax, enjoy views & game room.

3 bedrooms, 5 beds, 2.5 private bathrooms

15–20 Oct

£1,284 total

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4.94 out of 5 average rating, 70 reviews

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Guest favourite

Cottage in St. Leonard

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

2 bedrooms, 4 beds, 1.5 bathrooms

12–17 Oct

Extended stay discount

Free cancellation

4.92 out of 5 average rating, 202 reviews

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Guest favourite

Home in St. Leonard

Shewells Cottage at Long Beach

3 bedrooms, 6 beds, 1 bathroom

4–9 Oct

£570 total

5.0 out of 5 average rating, 9 reviews

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Guest favourite

Home in St. Leonard

Hickory House on the Chesapeake Bay!

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

4.91 out of 5 average rating, 97 reviews

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Guest favourite

Flat in St. Leonard

The Loft at Flag Harbor

2 bedrooms, 3 beds, 1 bathroom

1–6 Oct

£1,020 total

Free cancellation

4.89 out of 5 average rating, 19 reviews

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Home in St. Leonard

Waterfront – Private Beach & Beautiful Water Views

4 bedrooms, 5 beds, 3 bathrooms

1–6 Oct

£1,593 total

New place to stay

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Guest favourite

Place to stay in St. Leonard

Mermaids Paradise

1 bedroom, 2 beds, 1 bathroom

2–7 Oct

£739 total

4.93 out of 5 average rating, 202 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

19–24 Oct

£3,252 total

4.96 out of 5 average rating, 90 reviews

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Guest favourite

Home in St. Leonard

Escape to the Bay~Waterfront

4 bedrooms, 6 beds, 4 bathrooms

15–21 May

£2,102 total

Free cancellation

4.92 out of 5 average rating, 37 reviews

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Guest favourite

Home in St. Leonard

Cozy Beach House ~Chesapeake Bay Getaway

3 bedrooms, 3 double beds, 1 bathroom

13–18 Oct

£983 total

4.85 out of 5 average rating, 80 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

11–16 Oct

£1,771 total

4.97 out of 5 average rating, 107 reviews

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Top guest favourite

Home in St. Leonard

Cottage on the Bay

2 bedrooms, 3 beds, 1 bathroom

13–18 Oct

£1,020 total

4.94 out of 5 average rating, 99 reviews

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Guest favourite

Home in St. Leonard

The Bay House at Long Beach

4 bedrooms, 5 beds, 2 bathrooms

1–6 Oct

£1,645 total

5.0 out of 5 average rating, 23 reviews

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Flat in St. Leonard

Highland Cow Apartment in St Leonard

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

New place to stay

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Cottage in St. Leonard

Spacious Beachfront Retreat w/Dock

5 bedrooms, 9 beds, 3 bathrooms

3–8 Oct

£2,488 total

4.82 out of 5 average rating, 145 reviews

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Guest favourite

Home in St. Leonard

Waterfront Home, Spectacular View & Private Beach!

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

£2,097 total

4.96 out of 5 average rating, 24 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

3–8 Oct

£826 total

4.69 out of 5 average rating, 134 reviews

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Top guest favourite

Home in St. Leonard

Cozy Cottage on the Chesapeake Bay

3 bedrooms, 6 beds, 2 bathrooms

13–18 Oct

£1,066 total

Free cancellation

4.92 out of 5 average rating, 199 reviews

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Cottage in Port Republic

Shewell’s Cottage by the Shore

3 bedrooms, 4 beds, 2 bathrooms

18–23 Oct

£783 total

4.79 out of 5 average rating, 221 reviews