Chilmark Beach House Rentals & Places to Stay

Find the best beach rentals in Chilmark - We found 37 exact matches

About Chilmark Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Chilmark? PickleTrip™ features more than 37 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Chilmark. Several of these vacation rentals in Chilmark 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 Chilmark.

PickleTrip™ Offers 37 holiday homes and places to stay in Chilmark. 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.

Show more
Show less

Frequently Asked Questions About Chilmark Beach Rentals

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

The average cost for a beach rental in Chilmark is $266 per night. PickleTrip has a wide assortment of great beachfront homes near Chilmark that would suit your needs.
Yes, we have 37 beach rentals with pools available in Chilmark. Check our search bar to find a selection of vacation rentals available near Chilmark.
Yes, here are the top beach rentals in Chilmark that allow you to bring your pet:

See all pet-friendly beach rentals in Chilmark 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 Chilmark to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 37 properties with private swimming pools or private homes with indoor pools in the Chilmark area.
About 37 properties in Chilmark boast of having access to hot tubs.