1. USA
  2. Maryland
  3. Chestertown
  4. Beach Home Rentals

Chestertown Beach House Rentals & Places to Stay

Find the best beach rentals in Chestertown - We found 18 exact matches

About Chestertown Beach Home Rentals on SunSkiResorts

Looking for a beach rental near Chestertown? SunSki features more than 18 beach rentals that are perfect for your next beach holiday. Discover luxury beach rentals within walking distance of Chestertown. Many of these vacation rentals in Chestertown are kid-friendly and family-friendly, and they are located near top local attractions, ensuring guests have an unforgettable travel experience. SunSki’s rental listings come in various shapes and sizes, catering to large groups, friends, couples, or wedding retreats in Chestertown.

SunSki offers 18 holiday homes and places to stay in Chestertown. The site provides unique Airbnb, VRBO, and SunSki-style accommodations to suit your trip or getaway with friends and family.

SunSki beachfront rentals provide you with the best travel experience, making it easy to find and book the perfect place to stay in the best destinations.

Show more
Show less

Frequently Asked Questions About Chestertown Beach Rentals

The average cost for a beach rental in Chestertown is $514 per night. SunSki has a wide assortment of great beachfront homes near Chestertown that would suit your needs.
Yes, we have 18 beach rentals with pools available in Chestertown. Check our search bar to find a selection of vacation rentals available near Chestertown.
Yes, here are the top beach rentals in Chestertown that allow you to bring your pet:

See all pet-friendly beach rentals in Chestertown on SunSkiResorts

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Chestertown to find one that works for you.
As of 2025, the data from SunSkiResorts shows that there are over 18 properties with private swimming pools or private homes with indoor pools in the Chestertown area.
About 18 properties in Chestertown boast of having access to hot tubs.