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Search results; 722 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

$2,170 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

17–22 Jul

$1,975 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Home in Charlestown

The Cooper House in Charlestown, MD

4 bedrooms, 6 beds

26–31 Jul

$4,587 SGD for 5 nights

4.99 out of 5 average rating, 87 reviews

Guest favourite

Home in Charlestown

The Sunset House-Hot Tub-Sauna

5 bedrooms, 5 beds

5–10 Aug

$2,645 SGD for 5 nights

4.95 out of 5 average rating, 83 reviews

Superhost

Home in Charlestown

Stay Blue Heron, Coastal Comfort in Charlestown.

4 bedrooms, 5 beds

19–24 Jul

$2,365 SGD for 5 nights

4.2 out of 5 average rating, 5 reviews

Guest favourite

Home in North East

Waterfront Historical District Home Near River

3 bedrooms, 4 beds

5–10 Aug

$2,164 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Cottage in Charlestown

Charlestown Cottage at Cattail Bend

2 bedrooms, 3 beds

11–16 Jul

$1,849 SGD for 5 nights

4.85 out of 5 average rating, 109 reviews

Home in Charlestown

Cozy cape cod in water oriented Community near I95

3 bedrooms, 3 beds

18–23 Aug

$1,182 SGD for 5 nights

Free cancellation

4.84 out of 5 average rating, 115 reviews

Top guest favourite

Room in Charlestown

"Sunrise on the River"

2 beds

11–16 Jul

$1,203 SGD for 5 nights

4.99 out of 5 average rating, 98 reviews

Top guest favourite

Home in Perryville

Upper Chesapeake Getaway

3 bedrooms, 6 beds

30 Aug – 4 Sept

$2,101 SGD for 5 nights

4.98 out of 5 average rating, 161 reviews

Top guest favourite

Cottage in Charlestown

Long Beach Cottage, Hot Tub, Beachfront

1 bedroom, 1 king bed

20–25 Sept

$3,191 SGD for 5 nights

4.96 out of 5 average rating, 281 reviews

Top guest favourite

Home in North East

Boho River Cottage

2 bedrooms, 3 beds

25–30 Jul

$1,561 SGD for 5 nights

4.98 out of 5 average rating, 80 reviews

Top guest favourite

Home in North East

Riverfront Haven @ Hances Point

4 bedrooms, 7 beds

8–13 Jul

$4,828 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Cottage in Charlestown

Key West Cottage in Charlestown, MD

3 bedrooms, 4 beds

18–23 Jul

$2,326 SGD for 5 nights

4.92 out of 5 average rating, 25 reviews

Guest favourite

Home in Perryville

Top of the Chesapeake - Private Waterfront Home

5 bedrooms, 8 beds

31 Aug – 5 Sept

$2,810 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 246 reviews

Top guest favourite

Cottage in North East

Persimmon Pastures

3 bedrooms, 3 beds

16–21 Aug

$1,009 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 690 reviews

Home in North East

Pool House by the North East River

3 bedrooms, 6 beds

26–31 Jul

4.67 out of 5 average rating, 33 reviews

Guest favourite

Home in North East

Spacious North East Home w/ Fenced Yard & Fire Pit

5 bedrooms, 6 beds

26–31 Jul

$2,523 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Home in Charlestown

Water View House in Charlestown, MD

4 bedrooms, 4 beds

18–23 Jul

$2,972 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews