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 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
Type of place
Show map
Search results; Over 1,000 homes in Chesterton
Over 1,000 homes in Chesterton
Top guest favourite
Guest favourite
Home in Chesterton
Hotel Whiskey
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
15–20 Aug
15–20 Aug
$1,479 SGD
Show price breakdown
for 5 nights
$1,479 SGD for 5 nights
,
·
4.97 out of 5 average rating, 181 reviews
4.97 (181)
Flat in Chesterton
Newly Redone Dunes Getaway
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,059 SGD
Show price breakdown
for 5 nights
$1,059 SGD for 5 nights
4.79 out of 5 average rating, 14 reviews
4.79 (14)
Guest favourite
Guest favourite
Home in Chesterton
South Shore Studio Apartment {National Park}
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
10–15 Aug
10–15 Aug
$1,184 SGD
Show price breakdown
for 5 nights
$1,184 SGD for 5 nights
4.83 out of 5 average rating, 418 reviews
4.83 (418)
Superhost
Superhost
Home in Chesterton
Dunes Home – Walk to Town, Fenced Yard, Near Dunes
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
7–12 Sept
7–12 Sept
$1,485 SGD
Show price breakdown
for 5 nights
$1,485 SGD for 5 nights
4.79 out of 5 average rating, 121 reviews
4.79 (121)
Top guest favourite
Guest favourite
Room in Westville
Nice house in safe neighborhood
2 queen beds
2 queen beds
16–21 Aug
16–21 Aug
$551 SGD
Show price breakdown
for 5 nights
$551 SGD for 5 nights
4.97 out of 5 average rating, 545 reviews
4.97 (545)
Guest favourite
Guest favourite
Guest house in Chesterton
"myhathouse" detached studio downtown Chesterton
1 bedroom
1 bedroom
,
·
2 beds
2 beds
8–13 Sept
8–13 Sept
$734 SGD
Show price breakdown
for 5 nights
$734 SGD for 5 nights
4.92 out of 5 average rating, 417 reviews
4.92 (417)
Guest favourite
Guest favourite
Room in Portage
Suburban living by Chicago/Dunes National Pk
1 queen bed
1 queen bed
30 Aug – 4 Sept
30 Aug – 4 Sept
$356 SGD
Show price breakdown
for 5 nights
$356 SGD for 5 nights
4.87 out of 5 average rating, 175 reviews
4.87 (175)
Guest favourite
Guest favourite
Flat in Valparaiso
The Comfort Lodge Apt 3
1 bedroom
1 bedroom
,
·
1 bed
1 bed
13–18 Sept
13–18 Sept
$627 SGD
Show price breakdown
for 5 nights
$627 SGD for 5 nights
4.75 out of 5 average rating, 48 reviews
4.75 (48)
Top guest favourite
Guest favourite
Home in Chesterton
Beautiful Vintage "Morgan-House"
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
8–13 Sept
8–13 Sept
$1,333 SGD
Show price breakdown
for 5 nights
$1,333 SGD for 5 nights
4.95 out of 5 average rating, 66 reviews
4.95 (66)
Guest favourite
Guest favourite
Hotel in Chesterton
Lake Michigan Room (204)
1 bedroom
1 bedroom
,
·
1 bed
1 bed
16–21 Aug
16–21 Aug
$959 SGD
Show price breakdown
for 5 nights
$959 SGD for 5 nights
4.88 out of 5 average rating, 24 reviews
4.88 (24)
Guest favourite
Guest favourite
Townhouse in Chesterton
South Shore Escape
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
16–21 Aug
16–21 Aug
$2,273 SGD
Show price breakdown
for 5 nights
$2,273 SGD for 5 nights
4.81 out of 5 average rating, 63 reviews
4.81 (63)
Guest favourite
Guest favourite
Home in Chesterton
Charming Old Town Retreat in the Heart of Duneland
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
13–18 Sept
13–18 Sept
$1,935 SGD
Show price breakdown
for 5 nights
$1,935 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favourite
Guest favourite
Flat in Chesterton
Chesterton Charmer: Upper Unit
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
16–21 Aug
16–21 Aug
$1,483 SGD
$1,026 SGD
Show price breakdown
for 5 nights
4.94 out of 5 average rating, 65 reviews
4.94 (65)
Top guest favourite
Guest favourite
Bungalow in Chesterton
Charming Country Cottage
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
13–18 Sept
13–18 Sept
$1,423 SGD
Show price breakdown
for 5 nights
$1,423 SGD for 5 nights
4.98 out of 5 average rating, 119 reviews
4.98 (119)
Top guest favourite
Guest favourite
Cottage in Valparaiso
Flint Lake Cottage.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,107 SGD
Show price breakdown
for 5 nights
$1,107 SGD for 5 nights
4.89 out of 5 average rating, 625 reviews
4.89 (625)
Top guest favourite
Guest favourite
Home in Valparaiso
Long Lake Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
23–28 Aug
23–28 Aug
$1,208 SGD
Show price breakdown
for 5 nights
$1,208 SGD for 5 nights
4.98 out of 5 average rating, 43 reviews
4.98 (43)
Top guest favourite
Guest favourite
Flat in Chesterton
Chesterton Charmer: Lower Unit
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$1,522 SGD
$1,151 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 78 reviews
4.96 (78)
Top guest favourite
Guest favourite
Flat in Portage
Trailside Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
16–21 Aug
16–21 Aug
$1,031 SGD
Show price breakdown
for 5 nights
$1,031 SGD for 5 nights
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Guest favourite
Guest favourite
Guest house in Valparaiso
Private Cottage in Gated Nudist Community
1 bed
1 bed
9–14 Aug
9–14 Aug
$528 SGD
Show price breakdown
for 5 nights
$528 SGD for 5 nights
4.95 out of 5 average rating, 227 reviews
4.95 (227)
1
2
3
4
…
15
