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 Chesterton
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
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Chesterton
Over 1,000 homes in Chesterton
Superhost
Superhost
Camper van/Motorhome in Chesterton
South Shore RV National Park.
1 bedroom
,
·
1 bed
,
·
1 private bathroom
20–25 Sept
20–25 Sept
$1,250 SGD
$628 SGD
Show price breakdown
for 5 nights
,
·
4.79 out of 5 average rating, 161 reviews
4.79 (161)
Guest favourite
Guest favourite
Flat in Chesterton
Chesterton Charmer: Upper Unit
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,268 SGD
$871 SGD
Show price breakdown
for 5 nights
4.93 out of 5 average rating, 69 reviews
4.93 (69)
Guest favourite
Guest favourite
Home in Chesterton
Beautiful Vintage "Morgan-House"
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$1,262 SGD
Show price breakdown
for 5 nights
$1,262 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 71 reviews
4.96 (71)
Top guest favourite
Guest favourite
Flat in Chesterton
Chesterton Charmer: Lower Unit
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
14–19 Sept
14–19 Sept
$1,390 SGD
$999 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 81 reviews
4.96 (81)
Top guest favourite
Guest favourite
Home in Chesterton
Retro 1950s Estate w Hot Tub Near Indiana Dunes
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
$3,183 SGD
$2,538 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 100 reviews
4.98 (100)
Flat in Chesterton
Newly Redone Dunes Getaway
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,170 SGD
$1,061 SGD
Show price breakdown
for 5 nights
4.75 out of 5 average rating, 16 reviews
4.75 (16)
Superhost
Superhost
Room in Valparaiso
The Cozy Nest
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
28 Nov – 5 Dec
28 Nov – 5 Dec
$457 SGD
Show price breakdown
for 7 nights
$457 SGD for 7 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Guest house in Chesterton
"myhathouse" detached studio downtown Chesterton
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$796 SGD
$694 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 422 reviews
4.92 (422)
Top guest favourite
Guest favourite
Flat in Portage
Trailside Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$1,015 SGD
Show price breakdown
for 5 nights
$1,015 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Guest favourite
Guest favourite
Home in Chesterton
The Tower Haus | Dune Trails + Hot Tub
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$2,238 SGD
$1,968 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Top guest favourite
Guest favourite
Bungalow in Chesterton
Charming Country Cottage
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,411 SGD
$1,239 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 128 reviews
4.98 (128)
Top guest favourite
Guest favourite
Home in Chesterton
Chesterton 3 Bedroom Home Away From Home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Oct
5–10 Oct
$1,455 SGD
$1,262 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Cottage in Valparaiso
Flint Lake Cottage.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,167 SGD
Show price breakdown
for 5 nights
$1,167 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 631 reviews
4.89 (631)
Top guest favourite
Guest favourite
Barn in Valparaiso
The Good Farm: Barn BnB on 44 acres near Lake Mich
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,525 SGD
$1,374 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 242 reviews
5.0 (242)
Guest favourite
Guest favourite
Home in Porter
The Porter Nook | Walk to Trails + Dining
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,119 SGD
Show price breakdown
for 5 nights
$1,119 SGD for 5 nights
5.0 out of 5 average rating, 43 reviews
5.0 (43)
Top guest favourite
Guest favourite
Guest house in Chesterton
Cozy Guest House with Pool near National Park
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
2–7 Oct
2–7 Oct
$1,271 SGD
Show price breakdown
for 5 nights
$1,271 SGD for 5 nights
4.97 out of 5 average rating, 106 reviews
4.97 (106)
Superhost
Superhost
Home in Chesterton
Dunes Home – Walk to Town, Fenced Yard, Near Dunes
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,256 SGD
$1,114 SGD
Show price breakdown
for 5 nights
Free cancellation
4.79 out of 5 average rating, 127 reviews
4.79 (127)
Guest favourite
Guest favourite
Home in Chesterton
South Shore Studio Apartment {National Park}
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$1,088 SGD
$771 SGD
Show price breakdown
for 5 nights
4.83 out of 5 average rating, 433 reviews
4.83 (433)
Superhost
Superhost
Home in Chesterton
Roomy Retreat–Family&Friends|2 King Beds|Game Room
5 bedrooms
5 bedrooms
,
·
13 beds
13 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,526 SGD
Show price breakdown
for 5 nights
$2,526 SGD for 5 nights
Free cancellation
4.8 out of 5 average rating, 105 reviews
4.8 (105)
1
2
3
4
…
15