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 Michigan City
4.95 out of 5 average rating, 399 reviewsLittle Copper Cabin
31 Mar – 7 Apr
$326 NZD per night
Guest favourite
Farm stay in De Motte
4.94 out of 5 average rating, 113 reviewsCozy barn loft on organic vegetable farm
17–24 Aug
$157 NZD per night
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 39 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
18–25 Feb
$277 NZD per night
Guest favourite
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
20–27 Dec
$273 NZD per night
Superhost
Home in Chesterton
4.88 out of 5 average rating, 42 reviewsDunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home
13–20 Jan
$322 NZD per night
Guest favourite
Home in Valparaiso
4.97 out of 5 average rating, 88 reviewsCozy Luxe Downtown Valparaiso Stay
17–24 Sep
$251 NZD per night
Guest favourite
Cottage in Valparaiso
4.96 out of 5 average rating, 49 reviewsCozy 2 Bedroom Valparaiso Cottage
16–23 Jun
$258 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
8–15 Apr
$264 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
- Rentals with a washing machine and dryer Chesterton
- Family-friendly rentals Chesterton
- Cabin rentals Chesterton
- Monthly Rentals Chesterton
- Rentals with a fire pit Chesterton
- House rentals Chesterton
- Rentals with a patio Chesterton
- Rentals with outdoor seating Chesterton
- Pet-friendly rentals Chesterton
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