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 Castletown
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; Over 1,000 homes in Castletown
Over 1,000 homes in Castletown
Hostel in Castletown
Portland Outdoor Centre Bunkhouse/Hostel Room 1
1 bedroom
,
·
6 beds
,
·
1 private bathroom
9–14 Aug
9–14 Aug
$1,382 SGD
Show price breakdown
for 5 nights
$1,382 SGD for 5 nights
,
·
4.64 out of 5 average rating, 33 reviews
4.64 (33)
Home in Dorset
Pink Cottage • Quirky Coastal Near Chesil Beach
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Sept
5–10 Sept
$1,490 SGD
Show price breakdown
for 5 nights
$1,490 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Dorset
Sea and Sun
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$2,361 SGD
Show price breakdown
for 5 nights
$2,361 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Bungalow in Dorset
Islands Wrest (The Galleon Rm). Pet friendly.
1 bed
1 bed
,
·
1 bathroom
1 bathroom
24–29 Sept
24–29 Sept
$679 SGD
Show price breakdown
for 5 nights
$679 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 248 reviews
4.95 (248)
Guest favourite
Guest favourite
Home in Dorset
Truly a little hideaway near the beach
1 bedroom
1 bedroom
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
11–16 Jan
11–16 Jan
$907 SGD
Show price breakdown
for 5 nights
$907 SGD for 5 nights
4.88 out of 5 average rating, 33 reviews
4.88 (33)
Guest favourite
Guest favourite
Home in Dorset
Fair Winds House
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1.5 bathrooms
1.5 bathrooms
14–19 Oct
14–19 Oct
$1,151 SGD
$1,010 SGD
Show price breakdown
for 5 nights
Free cancellation
4.86 out of 5 average rating, 204 reviews
4.86 (204)
Top guest favourite
Guest favourite
Place to stay in Portland
Beautiful Modern Room Near the Sea
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$934 SGD
$821 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 155 reviews
4.99 (155)
Top guest favourite
Guest favourite
Cottage in Fortuneswell
Maidenwell Cottage. Near Chesil Beach, Portland
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,344 SGD
$1,193 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 333 reviews
4.99 (333)
Guest favourite
Guest favourite
Cottage in Dorset
Chesil Cove Holiday Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
$815 SGD
Show price breakdown
for 5 nights
$815 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 194 reviews
4.89 (194)
Guest favourite
Guest favourite
Home in Dorset
April's Cottage, sea views close to Chesil Beach
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
30 Sept – 5 Oct
30 Sept – 5 Oct
$1,229 SGD
$1,078 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 269 reviews
4.92 (269)
Guest favourite
Guest favourite
Flat in Easton
Large 3 bedroom Coastal apartment
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$1,716 SGD
$1,506 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favourite
Guest favourite
Room in Dorset
1st Private room in Shared house mid renovation
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$649 SGD
$570 SGD
Show price breakdown
for 5 nights
Free cancellation
4.9 out of 5 average rating, 132 reviews
4.9 (132)
Guest favourite
Guest favourite
Home in Dorset
Spacious 'Midway' by the Sea in Fortuneswell
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,504 SGD
$1,333 SGD
Show price breakdown
for 5 nights
Free cancellation
4.86 out of 5 average rating, 37 reviews
4.86 (37)
Guest favourite
Guest favourite
Cottage in Fortuneswell
Cove Garden Cottage with enclosed sea view garden
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
18–23 Dec
18–23 Dec
$1,341 SGD
$1,193 SGD
Show price breakdown
for 5 nights
Free cancellation
4.88 out of 5 average rating, 160 reviews
4.88 (160)
Guest favourite
Guest favourite
Flat in Fortuneswell
Cobblers retreat
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
23–28 Sept
23–28 Sept
$992 SGD
$888 SGD
Show price breakdown
for 5 nights
Free cancellation
4.8 out of 5 average rating, 182 reviews
4.8 (182)
Guest favourite
Guest favourite
Tiny home in Portland
Coast - White Stones Studios
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,173 SGD
$1,033 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 310 reviews
4.95 (310)
Guest favourite
Guest favourite
Home in Dorset
Mum’s place
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
2–7 Sept
2–7 Sept
$3,007 SGD
$2,657 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Top guest favourite
Guest favourite
Room in Portland
Double room near to Chesil Cove beach
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
23–28 Sept
23–28 Sept
$354 SGD
$311 SGD
Show price breakdown
for 5 nights
Free cancellation
4.89 out of 5 average rating, 607 reviews
4.89 (607)
Guest favourite
Guest favourite
Room in Grove
Portland Tranquility and Adventure.
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Aug
16–21 Aug
$762 SGD
$672 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 44 reviews
4.98 (44)
1
2
3
4
…
15