Great Oak Manor Bed & Breakfast on the Chesapeake Bay

10568 Cliff Road, Chestertown, Maryland 21620
Innkeeper(s): Holly McKee
  • Escape to Great Oak Manor

    There is a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Located minutes away from Chestertown, Great Oak Manor is a magnificent country estate built in the Georgian Style. It is a charming Bed and Breakfast with twelve guest rooms and a fabulous family style accommodation in addition to spacious common areas.

    Whether you want to be active or simply to relax the options are plentiful. Take a bicycle ride on safe country roads, or explore the water from our private beach by kayak, paddle board, or canoe. Walk from our beach to the marina next door where you have access to a swimming pool, a fitness center, and a nine-hole golf course.

    To slow down, relax in a hammock shaded by stately old walnut trees, sit by the bay in an Adirondack chair or stroll the expansive lawn.

    Be sure not to miss our spectacular sunsets!


    Great Oak Manor Bed & Breakfast on the Chesapeake Bay Lake and sunset

  • General Information and Reservation Policies


    ***If you have any questions, call us at 410-778-5943 and we will gladly explain.***

    Great Oak Manor Bed & Breakfast on the Chesapeake Bay sunset back yard hammock

    Before Your Arrival:

    • We require a one night’s deposit at the time of booking to hold the room.
    • For groups or events we will discuss an appropriate amount for a depositupon booking.
    • A combined sales and lodging tax of 11% (6% MD and 5% Lodging) will be in addition to ournightly rates and applied to your total upon booking.
    • You will receive an email confirmation from us with details about your stay, a reminder of check-in and out times, and of our cancellation policy.
    • Rates are always quoted for two people and vary according to the day of the week and the season.
    • During our peak season (Mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.
    • We do release the 2 night minimum policy the Wednesday prior, so always be sure to check our availability as single nights are sometimes available.

    Pet Policies

    • We are a pet-friendly B&B and just ask that you let us know in advance if you plan on bringing your pet for the duration of your stay
    • The Sterling Suite, Roese Suite and Caulk are our 3 Pet-Friendly rooms
    • $25 fee per pet per night of the stay

    Check-In Policies and Arrival Information:

    • Check-in times are from 3pm – 7pm in Summer and 3pm – 6pm in Winter. Wecannot accept early check-ins.
    • Should you need to arrive later than 7pm, please let us know ahead of time so that we may inform you of our late check-in procedures.
    • Upon your arrival, we will give you a tour of the first floor, settle any remaining balances on your bill, and take you to your room.
    • We have a list of restaurant recommendations in each of the rooms and will be happy to make any reservations for you.
    • Afternoon refreshments will be available during check-in time.

    Check-Out Policies:

    • Check-out time is at 11 AM.However, as long as the room is vacated, we invite you to enjoy the grounds a while longer if you’d like.
    • Keys should be left in the room or brought down to the front desk.
    • If personal items are left behind, we will charge your provided credit card for shipping. After 30 days, all unclaimed items will be donated.

    Cancellation Policy:

    • Due to the small number of rooms we have, cancellations and shortened stays can affect us greatly. Reservations canceled before arrival for any reason, will be refunded any deposit less a $35 booking fee per room reserved.
    • Any groups or weddings: cancellation must be made 90 days prior to the event to receive any refund whatsoever. Balance will be due in full for any cancellations less than 90 days. The site fee policy is different and stated in the contract.
    • Reservations shortened or canceled 30 days or less will be responsible for one night at the highest rate if we cannot re-book the room.
    • No refunds for early departures and all refunds will be paid within 10 business days.

    General Information:

    • If you intend to order a package or room-add on, please allow up to 72 hours notice.
    • Fireplace season is November 1 – April 1
    • The Sterling and Russell Suite can hold up to 4 guests. The Roese suite can hold 3.
    • We are able to amend our breakfast options to suit dietary allergies and restrictions. Please let us know if you require anything before your arrival.
    • All rooms have WIFI (most of the time), DirecTV and flatscreen TV’s, private baths, and heating/air-conditioning.