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 seating area
  • Caulk Room bed at our Eastern Shore bed and breakfast
  • Caulk room seating area and TV
  • 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
Fireside Dinners at Great Oak Manor

Getaway to the Bay

Day One – Arrive & Unwind

  • Arrive at 1pm for an early check-in and be welcomed with a chilled bottle of Pinot Gris and a cheese and charcuterie board prepared by our chef.
  • Take a stroll around the property and down to our private beach. In season, we provide kayaks, paddle boards and a canoe for exploring Fairlee Creek and out into the Chesapeake Bay.
  • Freshen up and come to our dining room for a private, romantic dinner for two including a bottle of Crow Vineyard wine. Your special dinner will be prepared by our chef to your liking.

Day Two – Explore & Savor

  • Enjoy a scrumptious breakfast either in our safe dining room or in your own room complete with our signature Bloody Mary.
  • Pick up your picnic lunch to take with you while you explore Chestertown and Kent County. Your TouchStay App will guide you.
  • Savor dinner out at one of our top restaurants. We will supply a $100 voucher to use.

Day Three – Fuel Up & Head Home

  • Wake to another full breakfast in the dining room or in your room complete with a sunny Mimosa.
  • Take advantage of late check-out at noon and leave with a bag of our homemade manor house cookies for your trip home.

Price: $550

New reservations only. Cannot be combined with any other offers or third party specials. Room not included in package price.