The water calls you from your own private lookout of the Chesapeake Bay. Enjoy this spacious room with a luxurious king-size bed and a private bath that boasts walls the color of the sunsets, an inviting, rich red. Situated on the corner of the house on the second floor, the Caulk has an open feel and ample natural lighting from the waterfront windows.

Our romantic Chestertown bed and breakfast offers incredible Eastern Shore romantic getaways. Book a stay in our Caulk room today!

  • Caulk Room sitting area at our Chestertown bed and breakfast
  • Caulk Room bed at our Eastern Shore bed and breakfast
  • Caulk Room bathroom at our Cheaspeake Bay bed and breakfast
  • Outdoor table with full breakfast at our Cheaspeake Bay bed and breakfast

Amenities include:

  • King bed
  • Second floor
  • Private bath
  • Balcony
  • Bay views
  • Central heating/cooling
  • Pet friendly
Military combat boots with flags
Special

Veterans Special

As a special thank you for all that you’ve done, we would like to offer 20% off your entire stay.