Share this page

Relax at the Widow’s Walk Inn

Located in historic Chestertown on Maryland’s upper eastern shore, Widow’s Walk Inn provides comfortable lodging in its five rooms with the warm atmosphere of a family home. Whether you play a game or read a book in the parlor or relax in a rocking chair on one of the inn’s four porches, Widow’s Walk Inn offers plenty of opportunities to sit back and relax. Or you can venture out into the city to explore all that Chestertown has to offer!


Widow’s Walk Inn puts you at the heart of historic Chestertown, Maryland, a neighborhood of colonial homes in a town with over 300 years of American history behind it.


The comfortable atmosphere at Widow’s Walk Inn is perfect for your romantic getaway. Take an afternoon walk just down the street to Fountain Park or sit on a porch swing and enjoy a quiet moment.

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 5 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Chestertown, Maryland
  • Nearby Water Chester River
  • Open Dates All Year

Nearest Airports

  • Phillips Army Air Field (APG) / 18.4 miles
  • Lee Airport (ANP) / 32.6 miles
  • Baltimore/Washington International Thurgood Marshal Airport (BWI) / 32.2 miles

* Not all airports listed here may be open to public use, or service commercial flights

Additional Information

Room Amenities
  • Air Conditioning
Languages Spoken
  • English
402 High Street Chestertown, Maryland 21620 United States  
Rates From


Phone Number


Send an



No problem! Select the type of inquiry you'd like to send, enter your comments, and we'll make sure the property gets it.

By clicking 'Submit' you are agreeing to our Terms of Service

Vacation Request Successfully submitted. Thank You!