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 sitting room at our Eastern Shore bed and breakfast
  • Sterling Suite offers exceptional Eastern Shore getaways
  • 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
Glass of white wine in a vineyard

White Wines

As three-year winners of gold status at international competitions and the Maryland Governor’s Cup status, Crow Vineyard takes their wine seriously, just like we know you will seriously enjoy these local wines!