Aerial view of ships at the Downrigger Sailing Event in Chestertown, MD

Chestertown

Are you headed to Chestertown to experience this charming and quaint community on Maryland’s Eastern Shore? Eastern Shore Vacation Rentals has you covered. Our Chestertown, MD, vacation rentals are perfect for people visiting from the Philadelphia area or for those of you who simply want to try a new place to vacation on the Eastern Shore. 

View our Chestertown, MD rentals today and get one step closer to the ultimate Eastern Shore getaway. Plus, keep in mind that we are constantly adding new house rentals to our portfolio. Make sure to check back often for new properties!

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Special Offer! Thornton FROM $4500 - $6000

Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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