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Search results; 726 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

$2,171 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

$1,817 SGD for 5 nights

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Room in Charlestown

"Sunrise on the River"

2 beds

11–16 Jul

$1,204 SGD for 5 nights

4.99 out of 5 average rating, 98 reviews

Guest favourite

Home in Charlestown

The Sunset House-Hot Tub-Sauna

5 bedrooms, 5 beds

29 Jul – 3 Aug

$2,646 SGD for 5 nights

4.95 out of 5 average rating, 84 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

Top guest favourite

Cottage in Charlestown

Long Beach Cottage, Hot Tub, Beachfront

1 bedroom, 1 king bed

20–25 Sept

$3,192 SGD for 5 nights

4.96 out of 5 average rating, 281 reviews

Top guest favourite

Home in Charlestown

The Cooper House in Charlestown, MD

4 bedrooms, 6 beds

26–31 Jul

$4,570 SGD for 5 nights

4.99 out of 5 average rating, 87 reviews

Superhost

Home in Charlestown

Stay Blue Heron, Coastal Comfort in Charlestown.

4 bedrooms, 5 beds

19–24 Jul

$2,316 SGD for 5 nights

4.2 out of 5 average rating, 5 reviews

Superhost

Home in Charlestown

Long Beach Wellness Retreat Hot tub/Sauna/Plunge

1 bedroom, 3 beds

23–28 Aug

$4,819 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

$2,102 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

$1,525 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

$2,164 SGD for 5 nights

5.0 out of 5 average rating, 15 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

Cabin in North East

Bayview Cottage

2 bedrooms, 2 queen beds

10–15 Jul

$1,942 SGD for 5 nights

4.89 out of 5 average rating, 66 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

Guest favourite

Cottage in Port Deposit

The River Cottage

1 bedroom, 3 beds

26–31 Jul

$1,485 SGD for 5 nights

4.94 out of 5 average rating, 343 reviews

Top guest favourite

Home in North East

Riverfront Haven @ Hances Point

4 bedrooms, 7 beds

11–16 Jul

$4,598 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Cabin in North East

Waterfront Cabin on the Chesapeake

3 bedrooms, 3 beds

10–15 Jul

$3,389 SGD for 5 nights

4.97 out of 5 average rating, 196 reviews

Superhost

Flat in North East

Unique Farm Stay At Peach Place

1 bedroom, 2 beds

12–17 Jul

$1,486 SGD for 5 nights

New place to stay