The king-size bed in the Tylden room at our Eastern Shore B&B is the perfect place to curl up and read a book as you gaze out at the Bay. A small iron Juliet-type balcony outside the door provides a serene spot to watch the sun set over the water, or to just gaze out and watch the squirrels and boats. Tylden features a stand-alone shower in its private bath.

  • Tylden Room offers incredible Eastern Shore romantic getaways
  • Tylden Room bed and seating area at our Chestertown, MD B&B
  • Outdoor table at our Chestertown, MD B&B set for breakfast
  • Our Beach with chairs and a canoe

Amenities include:

  • King bed
  • Second floor
  • Private bath
  • Juliet Balcony
  • Bay views
  • Heating/cooling
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.