We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; 702 homes in Charlestown

Guest favourite

Home in Charlestown

The Sunset House-Hot Tub-Sauna

5 bedrooms, 5 beds, 3 bathrooms

23–28 Aug

$2,498 SGD for 5 nights

4.94 out of 5 average rating, 86 reviews

Top guest favourite

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

1 bedroom, 1 king bed, 1 bathroom

20–25 Sept

$3,163 SGD for 5 nights

4.96 out of 5 average rating, 291 reviews

Top guest favourite

Home in Charlestown

The Cooper House in Charlestown, MD

4 bedrooms, 6 beds, 4 bathrooms

29 Aug – 3 Sept

$4,347 SGD for 5 nights

4.99 out of 5 average rating, 91 reviews

Superhost

Home in Charlestown

Stay Blue Heron, Coastal Comfort in Charlestown.

4 bedrooms, 5 beds, 3.5 bathrooms

16–21 Aug

4.5 out of 5 average rating, 10 reviews

Top guest favourite

Home in Charlestown

Catching Sunsets on the Bay

3 bedrooms, 3 beds, 2.5 bathrooms

21–26 Aug

$1,998 SGD for 5 nights

4.99 out of 5 average rating, 81 reviews

Guest favourite

Home in Charlestown

Long Beach Wellness Retreat Hot tub/Sauna/Plunge

1 bedroom, 2 beds, 1 bathroom

4–9 Oct

$3,137 SGD for 5 nights

5.0 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

$1,812 SGD for 5 nights

4.86 out of 5 average rating, 112 reviews

Top guest favourite

Room in Charlestown

"Sunrise on the River"

2 beds, 1 bathroom

15–20 Aug

$1,193 SGD for 5 nights

4.99 out of 5 average rating, 102 reviews

Top guest favourite

Cottage in North East

Persimmon Pastures

3 bedrooms, 3 beds, 1 bathroom

7–12 Nov

$963 SGD for 5 nights

4.98 out of 5 average rating, 701 reviews

Guest favourite

Home in Perryville

Upper Chesapeake Getaway

3 bedrooms, 6 beds, 1.5 bathrooms

30 Aug – 4 Sept

$2,046 SGD for 5 nights

4.96 out of 5 average rating, 167 reviews

Guest favourite

Guest house in Elkton

Countryside-Stablehouse-Cozy for 2-Autumn Getaway!

1 bedroom, 1 king bed, 1 bathroom

23–28 Aug

$870 SGD for 5 nights

4.92 out of 5 average rating, 203 reviews

Superhost

Flat in Perryville

Back Bay Retreat

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

$1,427 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Perryville

Waldins Chesapeake

3 bedrooms, 3 beds, 1.5 bathrooms

30 Aug – 4 Sept

$2,717 SGD for 5 nights

4.9 out of 5 average rating, 10 reviews

Guest favourite

Cottage in Charlestown

Key West Cottage in Charlestown, MD

3 bedrooms, 4 beds, 2 bathrooms

16–21 Aug

$2,209 SGD for 5 nights

4.92 out of 5 average rating, 25 reviews

Top guest favourite

Cottage in Port Deposit

The River Cottage

1 bedroom, 3 beds, 1 bathroom

23–28 Aug

$1,441 SGD for 5 nights

4.94 out of 5 average rating, 353 reviews

Home in Charlestown

Cozy cape cod in water oriented Community near I95

3 bedrooms, 3 beds, 1 bathroom

15–20 Sept

$1,220 SGD for 5 nights

4.84 out of 5 average rating, 119 reviews

Top guest favourite

Home in North East

Boho River Cottage

2 bedrooms, 3 beds, 1 bathroom

27 Sept – 2 Oct

4.98 out of 5 average rating, 84 reviews

Guest favourite

Home in North East

Unique Farm Stay At Peach Place

1 bedroom, 2 beds, 1 bathroom

16–21 Aug

$1,441 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews