Chesterman Beach Rentals & Places to Stay

Find the best beach rentals in Chesterman Beach - We found 136 exact matches

About Chesterman Beach Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Chesterman Beach? PickleTrip™ features more than 136 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Chesterman Beach. Several of these vacation rentals in Chesterman Beach 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 Chesterman Beach.

PickleTrip™ Offers 136 holiday homes and places to stay in Chesterman Beach. 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 Chesterman Beach Beach Rentals

There are a lot of options in Chesterman Beach. If you plan on staying in the Chesterman Beach 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 Chesterman Beach:

The average cost for a beach rental in Chesterman Beach is $407 per night. PickleTrip has a wide assortment of great beachfront homes near Chesterman Beach that would suit your needs.
Yes, we have 136 beach rentals with pools available in Chesterman Beach. Check our search bar to find a selection of vacation rentals available near Chesterman Beach.
Yes, here are the top beach rentals in Chesterman Beach that allow you to bring your pet:

See all pet-friendly beach rentals in Chesterman Beach 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 Chesterman Beach to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 136 properties with private swimming pools or private homes with indoor pools in the Chesterman Beach area.
About 136 properties in Chesterman Beach boast of having access to hot tubs.