Gorgeous Chestertown House Rentals on the Eastern Shore

ESVR is now cultivating a portfolio of fine vacation house rentals in the Chestertown area! Perfect for our guests coming from the Philadelphia area or for those that just want to try a new place to vacation on the Eastern Shore. These rental properties offer privacy and the chance to explore the charming and quaint town of Chestertown, Maryland. We are constantly adding new house rentals to our Chestertown portfolio, so make sure to check back often for new properties.

Book your Chestertown, MD rental today and browse our available properties below. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

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Creek Cottage
Centreville, MD
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Creek Cottage
  • Pets Allowed
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Starting at (USD)


Thornton Farm - Grace and Elegance
Chestertown, MD
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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