Ship Watch Inn

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Ship Watch Inn Charming Chesapeake City Inn that offers waterfront view in all guest rooms. All the rooms are furnished with new flat screen tvs & free wifi.
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Originally built in the 1920's as a residence, the Inn was converted into a Bed and Breakfast in 1996. Furnished with antiques from the 1800's, the Inn features the warmth and charm of a southern b&b with the amenities and service of a modern day hotel.

10/13/2026

A Little Piece of Chesapeake City History Stopped By Today! ☕️🎱
Our building has worn many hats over the years. Back in 1833, it was built as the home of Captain Kendall Cropper (who, along with his three brothers, was instrumental in founding our town). Since then, these walls have housed a tinsmith’s shop, a post office, a gift shop, and today, Café on the Bay!
In between all of that, back in the 1960s, this very location was a pool hall—and today we had the absolute pleasure of welcoming Bill and Linda Harris for lunch! Mr. Harris used to run the pool hall. He shared with us that he used his earnings to pay for date nights with Mrs. Harris back when they were young. They even lived right next door on the second floor of the Ship Watch Inn for just $75 a month!
It is always such a joy hearing the rich history, memories, and love stories tied to this building and our town. Thank you so much to Mr. and Mrs. Harris for stopping by and sharing your story with us today!

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10/04/2026

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09/13/2026

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Donna Joy brought her mom for her annual birthday visit this weekend. 90 and still fabulous!Our guests came together to ...
09/13/2026

Donna Joy brought her mom for her annual birthday visit this weekend. 90 and still fabulous!

Our guests came together to sing and celebrate. Happy Birthday!!

⚓️ www.shipwatchinn.com

09/09/2026
Update: Both rooms have been claimed!Unexpected opening for Friday night with our 1st floor Somerset Queen room and 3rd ...
09/03/2026

Update: Both rooms have been claimed!

Unexpected opening for Friday night with our 1st floor Somerset Queen room and 3rd floor Caroline Queen room! Single night only. Call 410-885-5300 or reserve online at www.shipwatchinn.com ⚓️

Address

401 1st Street
Chesapeake City, MD
21915

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