Looking for places to stay in Chestertown, MD? Join us at our Eastern Shore pet-friendly hotel and stay in our romantic Sterling room. Life is sweet in this two-room accessible suite that has a separate sitting room and a bath with walk-in shower. Natural light covers every inch of this east-facing suite that overlooks the carriage house.

Inviting French doors beside the king-size bed lead to the garden, where you can meet the manor’s other guests: butterflies, birds, and squirrels. The Sterling’s private doors make it ideal for guests who choose to travel with pets and is one of three dog-friendly rooms.

Accessibility Features and Policies.

  • Sterling Suite offers exceptional Eastern Shore getaways
  • Sterling Suite sitting room at our Eastern Shore bed and breakfast
  • Sterling Suite bathroom at our Chesapeake Bay B&B
  • Breakfast Omelette

Amenities include:

  • King bed
  • First floor
  • Private bath
  • Two room suite
  • Sofa bed
  • Private entrance
  • Sunrise views
  • Pet friendly
  • Accessible
happy couple on their honeymoon
Package

Honeymoon Package

Start your happily ever after at our romantic Maryland bed and breakfast. Enjoy your stay with the following special details:

  • Two soft and luxurious Great Oak Manor bathrobes
  • Two exclusive pottery mugs to take home with you
  • A scrumptious breakfast served to you in-room, complete with Champagne