Our newest accommodation, the Carriage House at our Chestertown B&B is an exceptional Eastern Shore vacation rental. It boasts majestic views of Chesapeake Bay with room for up to 6 people.

The Carriage House has a full service kitchen equipped for all of your cooking needs. The master is the king bedroom. In the loft area you will find a queen bed. The Loft area also features a double and a twin fold out sleeper for extra guests.

  • The bedroom in our vacation rental on the Eastern Shore
  • Carriage House offers incredible Eastern Shore romantic getaways
  • The Carriage House offers exceptional weekend getaways from DC
  • Carriage House bathroom at our Chestertown, MD bed and breakfast
  • Carriage House living room at our Eastern Shore bed and breakfast
  • Carriage House bathroom at our Chestertown, MD vacation rental
  • Carriage House bedroom at our Chestertown B&B

Amenities include:

  • King & queen bed
  • Double & single sleeper sofa
  • Walk-in shower & claw foot soaking tub
  • Full kitchen
  • Wet bar & refrigerator
  • Sleeps up to 6 people
  • Bay views
Fireside Dinners at Great Oak Manor

Fireside Dinners

Feast on this decadent meal, including:

  • Seasonal Appetizer
  • Spinach or Caesar Salad
  • Your choice of two “Surf & Turf” entrées ~ Filet Mignon with Wild Mushroom Demi Glace, Our Own Jumbo Lump Crab Cake with Remoulade Sauce, Chicken Chesapeake, Vegetable Risotto
  • Rosemary Roasted Potato, Rice Pilaf, or Grilled Polenta
  • Roasted Green Beans with Shallots and Parmesan or Saute of Mixed Seasonal Vegetables in Herb Butter
  • Dessert
  • Beer & Wine Available for Purchase

Price: $150 per couple

Whenever possible, we strive to use fresh, local and/or organic products in support of our farmers and watermen.