Great Oak Manor Bed & Breakfast on the Chesapeake Bay

10568 Cliff Road, Chestertown, Maryland 21620
Innkeeper(s): Holly McKee
  • Anytime Specials

      Active Duty Military:

      As a small token of gratitude for all that you do, we always offer an additional 10% discount for all active duty military. Simply present your military ID upon check-in and mention this offer upon booking.

      Veterans Special:

      As a special thank you for all that you’ve done, we would like to offer a weekly special. Call to reserve your stay on any Tuesday or Wednesday and receive 20% your entire stay.

  • Room Add-Ons

    Price from: $40

      Cheese Anyone? - $40 or $60 (includes wine)

      Have a cheese and fruit tray ready and waiting for you in your room, or ask to have it delivered to you just in time to watch the sunset over the Bay.

      • Artisan cheeses
      • seasonal fruit
      • crackers
      • Fresh lemonade or bottle of wine

      Everyone Loves Flowers - $50

      Fresh flowers add a special touch of attention to show your partner or family member that you were thinking of them and just how much you care.

      • Beautifully arranged, waiting in your room

      Let’s Picnic - $50 or $70 (includes wine)

      Sometimes you arrive and don’t want to go back out for lunch or dinner. This way, you can enjoy a picnic meal on the beach, take it with you kayaking, or have a sunset picnic on the bluff.

      • Delicious fresh sandwiches with a choice of Chicken salad, Tuna Salad, Ham or Turkey & Cheese
      • Potato Chips
      • Homemade sweet snack of the day (cookies, brownies)
      • Fresh Fruit
      • Water, Iced tea, lemonade or bottle of wine
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