Holiday houses in Chesterton
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Top-rated holiday rentals in Chesterton
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton holiday rentals
Other great holiday rentals in Chesterton
Guest favourite
Cabin in Michiana
4.97 out of 5 average rating, 112 reviewsSteps to the beach at luxury cabin 1hr to Chicago
7 – 14 Apr
$1,919 AUD total
Guest favourite
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
15 – 22 Nov
$1,723 AUD total
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 40 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
17 – 24 Nov
$2,083 AUD total
Guest favourite
Home in Porter
5.0 out of 5 average rating, 31 reviewsDunes Woodland
19 – 26 Nov
$1,961 AUD total
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
23 Feb – 2 Mar
$2,068 AUD total
Guest favourite
Home in Valparaiso
4.97 out of 5 average rating, 88 reviewsCozy Luxe Downtown Valparaiso Stay
25 Sept – 2 Oct
$1,586 AUD total
Guest favourite
Home in Trail Creek
4.99 out of 5 average rating, 69 reviewsLeo Lodge
3 – 10 Mar
$1,345 AUD total
Guest favourite
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
16 – 23 Aug
$1,980 AUD total
Quick stats about accommodation in Chesterton
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
$15 AUD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- West Lafayette Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- Chicago Accommodation & holiday rentals
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