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Chesterton Beach House Rentals & Places to Stay

Find the best beach rentals in Chesterton - We found 27 exact matches

About Chesterton Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Chesterton? PickleTrip™ features more than 27 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Chesterton. Several of these vacation rentals in Chesterton are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Chesterton.

PickleTrip™ Offers 27 holiday homes and places to stay in Chesterton. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Chesterton Beach Rentals

There are a lot of options in Chesterton. If you plan on staying in the Chesterton area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Home Rentals in Chesterton:

The average cost for a beach rental in Chesterton is $272 per night. PickleTrip has a wide assortment of great beachfront homes near Chesterton that would suit your needs.
Yes, we have 27 beach rentals with pools available in Chesterton. Check our search bar to find a selection of vacation rentals available near Chesterton.
Yes, here are the top beach rentals in Chesterton that allow you to bring your pet:

See all pet-friendly beach rentals in Chesterton on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Chesterton to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 27 properties with private swimming pools or private homes with indoor pools in the Chesterton area.
About 27 properties in Chesterton boast of having access to hot tubs.