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Search results; 731 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

The Sunset House-Hot Tub-Sauna

5 bedrooms, 5 beds, 3 bathrooms

23–28 Aug

$2,515 SGD for 5 nights

4.95 out of 5 average rating, 84 reviews

Top guest favourite

Cottage in Charlestown

Long Beach Cottage, Hot Tub, Beachfront

1 bedroom, 1 king bed, 1 bathroom

20–25 Sept

$3,184 SGD for 5 nights

4.96 out of 5 average rating, 285 reviews

Guest favourite

Home in Charlestown

Catching Sunsets on the Bay

3 bedrooms, 3 beds, 2.5 bathrooms

21–26 Aug

$1,926 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 80 reviews

Top guest favourite

Home in Charlestown

The Cooper House in Charlestown, MD

4 bedrooms, 6 beds, 4 bathrooms

23–28 Aug

$4,189 SGD for 5 nights

4.99 out of 5 average rating, 89 reviews

Top guest favourite

Room in Charlestown

"Sunrise on the River"

2 beds, 1 bathroom

9–14 Aug

$1,170 SGD for 5 nights

4.99 out of 5 average rating, 100 reviews

Superhost

Home in Charlestown

Stay Blue Heron, Coastal Comfort in Charlestown.

4 bedrooms, 5 beds, 3.5 bathrooms

3–8 Aug

4.44 out of 5 average rating, 9 reviews

Guest favourite

Cottage in Charlestown

Charlestown Cottage at Cattail Bend

2 bedrooms, 3 beds, 1 bathroom

23–28 Aug

$1,657 SGD for 5 nights

4.86 out of 5 average rating, 112 reviews

Superhost

Home in Charlestown

Long Beach Wellness Retreat Hot tub/Sauna/Plunge

1 bedroom, 2 beds, 1 bathroom

27 Sept – 2 Oct

$3,454 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Port Deposit

Port Right Side *easy stay near 95* Port Deposit

3 bedrooms, 3 beds, 1 bathroom

2–7 Aug

4.87 out of 5 average rating, 118 reviews

Home in North East

Walk to Town & River: Charming Home in North East!

3 bedrooms, 5 beds, 3 bathrooms

2–7 Aug

4.89 out of 5 average rating, 19 reviews

Guest favourite

Cottage in Charlestown

Key West Cottage in Charlestown, MD

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

$2,224 SGD for 5 nights

4.92 out of 5 average rating, 25 reviews

Guest favourite

Home in North East

Waterfront Historical District Home Near River

3 bedrooms, 4 beds, 2 bathrooms

26–31 Aug

$2,159 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favourite

Guest suite in North East

The Cozy Studio of North East MD

2 beds, 1 bathroom

1–6 Aug

$709 SGD for 5 nights

4.92 out of 5 average rating, 159 reviews

Guest favourite

Home in Perryville

Upper Chesapeake Getaway

3 bedrooms, 6 beds, 1.5 bathrooms

30 Aug – 4 Sept

$2,052 SGD for 5 nights

4.96 out of 5 average rating, 163 reviews

Home in Chesapeake City

Floral Canal-Facing Hideaway

2 bedrooms, 4 beds, 1 bathroom

24–29 Aug

$1,582 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Home in North East

Spacious North East Home w/ Fenced Yard & Fire Pit

5 bedrooms, 6 beds, 3 bathrooms

23–28 Aug

$2,517 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Superhost

Home in North East

Family home w/game room, deck & hot tub

4 bedrooms, 4 beds, 3 bathrooms

17–22 Aug

Pay $0 today

Free cancellation

4.87 out of 5 average rating, 23 reviews

Top guest favourite

Flat in Havre de Grace

The Sappington House * easy stay near 95 * HdG

3 bedrooms, 3 beds, 1 bathroom

2–7 Aug

$1,160 SGD for 5 nights

4.92 out of 5 average rating, 50 reviews