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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

$1,474 SGD for 5 nights

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4.92 out of 5 average rating, 93 reviews

Top guest favourite

Cottage in St. Leonard

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

2 bedrooms, 4 beds

17–22 Aug

Extended stay discount

Free cancellation

4.94 out of 5 average rating, 194 reviews

Guest favourite

Home in St. Leonard

Escape to the Bay~Waterfront

4 bedrooms, 6 beds

10–16 Aug

$3,780 SGD for 6 nights

4.92 out of 5 average rating, 37 reviews

Guest favourite

Home in St. Leonard

Shewells Cottage at Long Beach

3 bedrooms, 6 beds

18–23 Aug

$1,295 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Flat in St. Leonard

The Loft at Flag Harbor

2 bedrooms, 3 beds

9–14 Aug

$1,682 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 18 reviews

Guest favourite

Home in St. Leonard

Cozy Beach House ~Chesapeake Bay Getaway

3 bedrooms, 3 double beds

15–20 Aug

$1,702 SGD for 5 nights

4.85 out of 5 average rating, 75 reviews

Home in St. Leonard

Large Spacious 5 Bedroom 8 Bed House at Long Beach

5 bedrooms, 8 beds

12–17 Aug

$1,721 SGD for 5 nights

4.72 out of 5 average rating, 131 reviews

Guest favourite

Guest suite in St. Leonard

Exclusive Waterfront Getaway

1 bedroom, 3 beds

5–10 Aug

4.94 out of 5 average rating, 35 reviews

Top guest favourite

Home in St. Leonard

Cottage on the Bay

2 bedrooms, 3 beds

31 Aug – 5 Sept

$1,639 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 95 reviews

Top guest favourite

Home in St. Leonard

Waterfront Home, Spectacular View & Private Beach!

3 bedrooms, 3 beds

9–14 Aug

4.95 out of 5 average rating, 19 reviews

Top guest favourite

Home in St. Leonard

Luxury Family: 5BR, Beach, GameRm, MovieRm, Kayaks

5 bedrooms, 8 beds

23–28 Aug

$6,866 SGD for 5 nights

4.95 out of 5 average rating, 85 reviews

Guest favourite

Home in St. Leonard

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

3 bedrooms, 5 beds

23–28 Aug

$2,609 SGD for 5 nights

4.96 out of 5 average rating, 67 reviews

Top guest favourite

Home in St. Leonard

Closest Home to Private Beach • Stunning Bay Views

3 bedrooms, 4 beds

31 Aug – 5 Sept

$2,553 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Home in St. Leonard

Waterfront! The River's Roost on the Patuxent!

3 bedrooms

14–19 Aug

$2,650 SGD for 5 nights

4.88 out of 5 average rating, 25 reviews

Guest favourite

Home in St. Leonard

OLD BAY beach-front classic on the Chesapeake Bay

3 bedrooms, 3 king beds

12–17 Aug

$4,770 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 59 reviews

Top guest favourite

Guest house in St. Leonard

Studio on the Bay.

1 bedroom, 1 queen bed

7–12 Aug

$1,191 SGD for 5 nights

4.97 out of 5 average rating, 123 reviews

Guest favourite

Cabin in St. Leonard

Beach Access Cozy Cedar Cottage

2 bedrooms, 2 queen beds

10–15 Aug

$1,490 SGD for 5 nights

4.95 out of 5 average rating, 95 reviews

Cottage in St. Leonard

Spacious Beachfront Retreat w/Dock

5 bedrooms, 9 beds

30 Aug – 4 Sept

$3,959 SGD for 5 nights

4.84 out of 5 average rating, 140 reviews

Guest favourite

Home in St. Leonard

The Bay House at Long Beach

4 bedrooms, 5 beds

9–14 Aug

$4,045 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 22 reviews