About Chestertown Maryland

Experience A Baycation in Chestertown!

Eastern Shore Vacation Rentals is now in the Chestertown Area! Feel free to browse our ever-growing portfolio of fine vacation homes located in Historic Chestertown and surrounding areas.  Many of our fine properties include waterfront locations, private swimming pools, and docks, as well as multiple acres of privacy to relax and enjoy your friends and family.  The perfect location for those looking for an easy destination within a few hours' drive from Philadelphia, Washington, DC, Virginia or other parts of Maryland, Chestertown is brimming with waterfront activities, bay beaches, seafood and many fine dining options, as well as historic sightseeing.  All of these activities are easy to enjoy when Eastern Shore Vacation Rentals provides a worry-free home base!  The pricing on our site is all-inclusive, meaning no additional fees for cleaning, linens, dogs (for dog-friendly homes only), security deposits and handling fees.  It's all included in the price!   And, all of our Chestertown vacation properties include direct check in and check out, so there is no need to come to the office for keys and waste time that could be spent enjoying your vacation time.

Start planning your Chestertown Vacation Today! Browse and book available vacation rentals today!