Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Charlestown
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; 725 homes in Charlestown
725 homes in Charlestown
Top guest favourite
Guest favourite
Serviced apartment in Charlestown
The Osprey Nest at the Cooper House
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
3–8 Jan
3–8 Jan
$2,170 SGD
Show price breakdown
for 5 nights
$2,170 SGD for 5 nights
,
·
4.93 out of 5 average rating, 56 reviews
4.93 (56)
Top guest favourite
Guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub, Beachfront
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$3,080 SGD
Show price breakdown
for 5 nights
$3,080 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 279 reviews
4.96 (279)
Guest favourite
Guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
17–22 Jul
17–22 Jul
$1,975 SGD
Show price breakdown
for 5 nights
$1,975 SGD for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 76 reviews
4.99 (76)
Guest favourite
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
16–21 Aug
16–21 Aug
$2,520 SGD
Show price breakdown
for 5 nights
$2,520 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 82 reviews
4.95 (82)
Top guest favourite
Guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
26–31 Jul
26–31 Jul
$4,585 SGD
Show price breakdown
for 5 nights
$4,585 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 87 reviews
4.99 (87)
Top guest favourite
Guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds
2 beds
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$1,203 SGD
Show price breakdown
for 5 nights
$1,203 SGD for 5 nights
4.99 out of 5 average rating, 98 reviews
4.99 (98)
Superhost
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
19–24 Jul
19–24 Jul
$2,380 SGD
Show price breakdown
for 5 nights
$2,380 SGD for 5 nights
Free cancellation
4.2 out of 5 average rating, 5 reviews
4.2 (5)
Superhost
Superhost
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
19–24 Aug
19–24 Aug
$5,097 SGD
Show price breakdown
for 5 nights
$5,097 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,304 SGD
Show price breakdown
for 5 nights
$2,304 SGD for 5 nights
4.98 out of 5 average rating, 160 reviews
4.98 (160)
Guest favourite
Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$1,848 SGD
Show price breakdown
for 5 nights
$1,848 SGD for 5 nights
4.85 out of 5 average rating, 109 reviews
4.85 (109)
Top guest favourite
Guest favourite
Home in North East
Boho River Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Jul
25–30 Jul
$1,561 SGD
Show price breakdown
for 5 nights
$1,561 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 80 reviews
4.98 (80)
Guest favourite
Guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Aug
5–10 Aug
$2,163 SGD
Show price breakdown
for 5 nights
$2,163 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Cottage in North East
Persimmon Pastures
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,008 SGD
Show price breakdown
for 5 nights
$1,008 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 688 reviews
4.98 (688)
Guest favourite
Guest favourite
Guest house in Elkton
Countryside-Stablehouse-Cozy for 2-Summer Getaway!
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
18–23 Jul
18–23 Jul
$966 SGD
Show price breakdown
for 5 nights
$966 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 193 reviews
4.91 (193)
Guest favourite
Guest favourite
Cottage in Port Deposit
The River Cottage
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
26–31 Jul
26–31 Jul
$1,485 SGD
Show price breakdown
for 5 nights
$1,485 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 343 reviews
4.94 (343)
Home in Charlestown
Cozy cape cod in water oriented Community near I95
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
18–23 Aug
18–23 Aug
$1,182 SGD
Show price breakdown
for 5 nights
$1,182 SGD for 5 nights
Pay $0 today
Free cancellation
4.84 out of 5 average rating, 115 reviews
4.84 (115)
Superhost
Superhost
Flat in North East
Unique Farm Stay At Peach Place
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,485 SGD
Show price breakdown
for 5 nights
$1,485 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in North East
Red Point Lighthouse
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
16–21 Jul
16–21 Jul
$4,547 SGD
Show price breakdown
for 5 nights
$4,547 SGD for 5 nights
4.96 out of 5 average rating, 132 reviews
4.96 (132)
Top guest favourite
Guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
6–11 Jul
6–11 Jul
$4,729 SGD
Show price breakdown
for 5 nights
$4,729 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 28 reviews
5.0 (28)
1
2
3
4
…
15