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Search results; 719 homes in Charlestown

Top guest favourite

Serviced apartment in Charlestown

The Osprey Nest at the Cooper House

2 bedrooms, 3 beds, 2 private bathrooms

3–8 Jan

$2,174 SGD for 5 nights

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4.93 out of 5 average rating, 56 reviews

Guest favourite

Home in Charlestown

Catching Sunsets on the Bay

3 bedrooms, 3 beds

27 Jul – 1 Aug

$1,863 SGD for 5 nights

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Cottage in Charlestown

Long Beach Cottage, Hot Tub, Beachfront

1 bedroom, 1 king bed

20–25 Sept

$3,196 SGD for 5 nights

4.96 out of 5 average rating, 281 reviews

Guest favourite

Home in Charlestown

The Sunset House-Hot Tub-Sauna

5 bedrooms, 5 beds

16–21 Aug

$2,524 SGD for 5 nights

4.95 out of 5 average rating, 83 reviews

Top guest favourite

Room in Charlestown

"Sunrise on the River"

2 beds

11–16 Jul

$1,205 SGD for 5 nights

4.99 out of 5 average rating, 98 reviews

Guest favourite

Cottage in Charlestown

Charlestown Cottage at Cattail Bend

2 bedrooms, 3 beds

11–16 Jul

$1,852 SGD for 5 nights

4.85 out of 5 average rating, 109 reviews

Superhost

Home in Charlestown

Stay Blue Heron, Coastal Comfort in Charlestown.

4 bedrooms, 5 beds

19–24 Jul

$2,351 SGD for 5 nights

4.2 out of 5 average rating, 5 reviews

Top guest favourite

Home in Charlestown

The Cooper House in Charlestown, MD

4 bedrooms, 6 beds

26–31 Jul

$4,576 SGD for 5 nights

4.99 out of 5 average rating, 87 reviews

Superhost

Home in Charlestown

Long Beach Wellness Retreat Hot tub/Sauna/Plunge

1 bedroom, 2 beds

23–28 Aug

$4,825 SGD for 5 nights

New place to stay

Top guest favourite

Home in Perryville

Upper Chesapeake Getaway

3 bedrooms, 6 beds

30 Aug – 4 Sept

$2,105 SGD for 5 nights

4.98 out of 5 average rating, 161 reviews

Top guest favourite

Home in North East

Boho River Cottage

2 bedrooms, 3 beds

25–30 Jul

$1,564 SGD for 5 nights

4.98 out of 5 average rating, 80 reviews

Guest favourite

Home in North East

Waterfront Historical District Home Near River

3 bedrooms, 4 beds

5–10 Aug

$2,167 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Top guest favourite

Cottage in North East

Persimmon Pastures

3 bedrooms, 3 beds

16–21 Aug

$1,007 SGD for 5 nights

4.98 out of 5 average rating, 691 reviews

Top guest favourite

Cottage in Charlestown

Key West Cottage in Charlestown, MD

3 bedrooms, 4 beds

18–23 Jul

$2,329 SGD for 5 nights

4.92 out of 5 average rating, 25 reviews

Top guest favourite

Home in North East

Riverfront Haven @ Hances Point

4 bedrooms, 7 beds

9–14 Jul

$4,823 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Room in Perryville

North River Hideaway | King Suite

1 king bed

8–13 Jul

$969 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favourite

Cabin in North East

Bayview Cottage

2 bedrooms, 2 queen beds

8–13 Jul

$1,945 SGD for 5 nights

4.89 out of 5 average rating, 66 reviews

Guest favourite

Cottage in Port Deposit

The River Cottage

1 bedroom, 3 beds

26–31 Jul

$1,487 SGD for 5 nights

4.94 out of 5 average rating, 343 reviews

Home in Charlestown

Cozy cape cod in water oriented Community near I95

3 bedrooms, 3 beds

18–23 Aug

$1,216 SGD for 5 nights

4.84 out of 5 average rating, 116 reviews