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
$304 NZD per night
Guest favourite
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
15–22 Nov
$273 NZD per night
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 40 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
17–24 Nov
$330 NZD per night
Guest favourite
Home in Porter
5.0 out of 5 average rating, 31 reviewsDunes Woodland
19–26 Nov
$311 NZD per night
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
23 Feb – 2 Mar
$323 NZD per night
Guest favourite
Home in Valparaiso
4.97 out of 5 average rating, 88 reviewsCozy Luxe Downtown Valparaiso Stay
25 Sep – 2 Oct
$251 NZD per night
Guest favourite
Home in Trail Creek
4.99 out of 5 average rating, 69 reviewsLeo Lodge
3–10 Mar
$213 NZD per night
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
$314 NZD per night
Quick stats about holiday rentals 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
$17 NZD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- West Lafayette Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Chicago Holiday rentals
- Kid-friendly rentals Chesterton
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- Rentals with a fire pit Chesterton
- Rentals with outdoor seating Chesterton
- Family-friendly rentals Chesterton
- Rentals with a patio Chesterton
- Pet-friendly rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
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