Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
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
Photo 1 of 6
Hostel in Castletown
Portland Outdoor Centre Bunkhouse/Hostel Room 14
1 bedroom
,
·
4 beds
,
·
1 shared bathroom
1–6 Sept
1–6 Sept
$958 SGD
Show price breakdown
for 5 nights
$958 SGD for 5 nights
,
·
4.68 out of 5 average rating, 19 reviews
4.68 (19)
Photo 1 of 6
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
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,349 SGD
$1,150 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 336 reviews
4.99 (336)
Photo 1 of 6
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
6–11 Oct
6–11 Oct
$337 SGD
$296 SGD
Show price breakdown
for 5 nights
Free cancellation
4.89 out of 5 average rating, 609 reviews
4.89 (609)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Dorset
Ope Gallery
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,739 SGD
$1,545 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 6
Guest favourite
Guest favourite
Townhouse in Dorset
CLOUD 9 🦚 Homely & Happy 😊 Near the Beach 🌊🐟🌞
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,398 SGD
Show price breakdown
for 5 nights
$1,398 SGD for 5 nights
4.95 out of 5 average rating, 301 reviews
4.95 (301)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Dorset
1GB Wifi | SuperKing bed | Sport TV | Washer/Dryer
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Sept
13–18 Sept
$1,669 SGD
Show price breakdown
for 5 nights
$1,669 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 51 reviews
4.98 (51)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Dorset
Pink Cottage • Quirky Coastal Near Chesil Beach
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,398 SGD
Show price breakdown
for 5 nights
$1,398 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Dorset
Sunset Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–7 Sept
1–7 Sept
$2,219 SGD
$1,657 SGD
Show price breakdown
for 6 nights
4.91 out of 5 average rating, 75 reviews
4.91 (75)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Dorset
Sea and Sun
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,526 SGD
Show price breakdown
for 5 nights
$1,526 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 6
Guest favourite
Guest favourite
Flat in Dorset
Chesil Beach View
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$975 SGD
Show price breakdown
for 5 nights
$975 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Photo 1 of 6
Guest favourite
Guest favourite
Cottage in Dorset
Chesil Cove Holiday Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
21–26 Oct
21–26 Oct
$921 SGD
$811 SGD
Show price breakdown
for 5 nights
Free cancellation
4.89 out of 5 average rating, 196 reviews
4.89 (196)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Dorset
Stone's Throw, Portland, on the Jurassic Coast
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$1,251 SGD
Show price breakdown
for 5 nights
$1,251 SGD for 5 nights
4.99 out of 5 average rating, 105 reviews
4.99 (105)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Portland
Light and airy attic room with kitchenette.
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$676 SGD
$596 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 187 reviews
4.99 (187)
Photo 1 of 6
Flat in Dorset
Spacious 2bed 2bath Chesil Beach & Sailing Academy
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
1–6 Sept
1–6 Sept
$1,821 SGD
Show price breakdown
for 5 nights
$1,821 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 6
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
$763 SGD
$675 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 254 reviews
4.95 (254)
Photo 1 of 6
Top 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
$1,017 SGD
Show price breakdown
for 5 nights
$1,017 SGD for 5 nights
Free cancellation
4.87 out of 5 average rating, 211 reviews
4.87 (211)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Portland
Pleasant en-suite room close to Chesil beach
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
21–26 Sept
21–26 Sept
$730 SGD
$642 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 75 reviews
4.99 (75)
Photo 1 of 6
Guest favourite
Guest favourite
Cottage in Dorset
Beach Views Cottage, Portland - Stunning & Cosy
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
21–26 Sept
21–26 Sept
$1,886 SGD
$1,669 SGD
Show price breakdown
for 5 nights
4.99 out of 5 average rating, 75 reviews
4.99 (75)
Photo 1 of 6
Guest favourite
Guest favourite
Cottage in Easton
Milly Moll Cottage, next to Church Ope Cove.
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Sept
25–30 Sept
$1,181 SGD
$1,044 SGD
Show price breakdown
for 5 nights
Free cancellation
4.91 out of 5 average rating, 267 reviews
4.91 (267)
1
2
3
4
…
15