A quiet and elegant inn nestled within the rich historical tapestry of Maryland's Chesapeake Bay region. Fully restored colonial inn nestled in the heart of downtown Chestertown.
Hours See website for hours.
231 High St.
Chestertown, MD
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  • Airport Shuttle
  • Breakfast Available
  • Free Breakfast
  • Free Parking
  • Free WiFi
  • Meeting Facilities
  • Number of Rooms
  • Weddings
Rated 5 by Terry K

September 02, 2023

Terry K


On a quick whim we decided to stay at the White Swan. We’ve been to Chestertown and love charm of the town but always simply a day trip. This time we decided to stay in town at the Tavern that always...

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Rated 5 by Guillaume926

June 13, 2023


Recipe for Romance

This historic B&B and town at the top of the Eastern Shore was the perfect setting for my wife and I to celebrate our 45th wedding anniversary. The tavern, with four rooms and two suites, has been...

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Rated 5 by Richard C

May 23, 2023

Richard C

Most charming Chestertown experience

This historic inn, which I have known for decades, has been beautifully refurbished and restored perfectly. It has all the charms of a colonial inn, but with completely modernized amenities, great...

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TripAdvisor Traveller Rating

Rated  based on 63 reviews
based on 63 Reviews
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