Great Oak Manor provides 12 comfortable suites and rooms with individual highlights such as a cozy fireplace, a spacious bath with skylight, and inviting French doors leading to the garden. Wake each morning to a full breakfast with seasonal fresh fruit, homemade baked goods, and views of Chesapeake Bay. Rates quoted are for double occupancy.

Accessibility Features and Policies.

Hynson

  • King bed
  • Third floor
  • Private bath
  • Bay views

Ringgold

  • King bed
  • Third floor
  • Private bath
  • Sunrise views

Geddes-Piper

  • King bed
  • Third floor
  • Private bath
  • Interior balcony
  • Bay views

Hodges

  • King bed
  • Second floor
  • Private bath
  • Fireplace
  • Sunrise views

Roese Suite

  • King bed
  • Second floor
  • Private bath
  • Two room suite
  • Fireplace

Russell Suite

  • King bed
  • Third floor
  • Private bath
  • Fireplace
  • Sunrise and bay views

Sterling Suite

  • King bed
  • First floor
  • Private bath
  • Private entrance
  • Accessible

Caulk

  • King bed
  • Second floor
  • Private bath
  • Balcony
  • Bay views

Tylden

  • King bed
  • Second floor
  • Private bath
  • Juliet Balcony
  • Bay views

Wickes

  • King bed
  • Second floor
  • Private bath
  • Fireplace
  • Sunrise views

D’Oench

  • King bed
  • Second floor
  • Private bath
  • Fireplace
  • Bay views

Marmaduke

  • King bed
  • Second floor
  • Private bath
  • Fireplace
  • Bay views

The Carriage House

  • King & queen bed
  • Walk-in shower
  • Claw foot tub
  • Kitchen
  • Bay views
  • Private
RoomGuestsBedBathFeaturesBook Room
Hynson Room bed and reading chair at our Chestertown B&B HynsonTwoKingTub/shower comboThird floor, Bay viewsCheck Rates
Ringgold Room bed, reading chair, and desk at our Chestertown bed and breakfast RinggoldTwoKingTub/shower comboThird floor, Sunrise viewsCheck Rates
Geddes-Piper Room offers exceptional weekend getaways from DC Geddes-PiperTwoKingTub/shower comboThird floor, Bay views, Interior balconyCheck Rates
Hodges Room bed and seating area at our bed and breakfast in Chestertown, MD HodgesTwoKingTub/shower comboSecond floor, sunrise views, fireplaceCheck Rates
Roese SuiteThreeKingTub/shower comboSecond floor, sunrise views, electric fireplace,Check Rates
Russell Suite bed and seating area with fireplace at our Chestertown, MD B&B Russell SuiteFourKingTub/shower comboThird floor, sunrise and bay views, fireplaceCheck Rates
Sterling Suite offers exceptional Eastern Shore getaways Sterling SuiteFourKingWalk-in showerFirst floor, sunrise views, private entrance, sofa bed, accessibleCheck Rates
The Caulk Room offers incredible Eastern Shore romantic getaways CaulkTwoKingTub/shower comboSecond floor, bay views, balcony,Check Rates
Tylden Room bed and seating area at our Eastern Shore B&B TyldenTwoKingWalk-in showerSecond floor, bay views, Juliet balconyCheck Rates
Wickes Room bed at our Eastern Shore Maryland bed and breakfast WickesTwoKingTub/shower comboSecond floor, sunrise views, fireplaceCheck Rates
D'Oench Room offers exceptional Chestertown, MD lodging D’OenchTwoKingTub/shower comboSecond floor, bay views, fireplaceCheck Rates
Marmaduke Room offers the ultimate romantic getaways near DC MarmadukeTwoKingTub/shower CombinationSecond floor, bay views, fireplaceCheck Rates
Our Eastern Shore vacation rental dining and living room The Carriage HouseSixKing & QueenWalk-in shower & claw foot tubBay views, kitchen,Check Rates

Crusier Bicycles in our front lawn

Stay in Comfort on Chesapeake Bay

At Great Oak Manor, on Maryland’s Eastern Shore we invite you to take full advantage of our comfortable accommodations. Enjoy breakfast in the Bay View Dining Room or outdoors in warm weather. Explore the collection of books in the Library. Relax in the Sunroom and savor a cup of tea or coffee. Nap in the hammocks or Adirondack chairs on the bluff.

In Suite we Offer:

  • Private bathrooms
  • Hair dryers
  • Flat screen, high-definition televisions
  • Cable Television
  • Fiber Optic WiFi
  • Bath Robes
  • Six guest rooms have fireplaces
    (fireplaces are operational from November 1 – April 1)

Amenities for Outside:

  • Cruiser bicycles
  • Kayaks, canoe, and paddle boards (in season)
  • Patio firepit
  • Private Chesapeake Bay beach access
  • 2 Electric Vehicle charging stations
  • Cornhole Games
  • Use of amenities at the marina next door:
    • Pool
    • Fitness room
    • 9-Hole golf course (bring your own clubs and balls)

General Information and Reservation Policies

Please be sure to read the fine print in anticipation of your visit. If you have any questions, please telephone the Manor at 410.778.5943 and we will gladly provide assistance.

General Information

  • Pets are prohibited.
  • Smoking is prohibited in the Manor.
  • Great Oak Manor is an adult property. Only children 18 years or older may accompany reserved adult guests.
  • We accept only registered Great Oak Manor Gift Certificates.
  • The Sterling and Russell Suite can accommodate up to 4 guests. The Roese suite can accommodate up to 3 guests.
  • Please let us know of your dietary preferences prior to your arrival.
  • All rooms have complimentary Wi-Fi access, private baths, and air-conditioning.
  • For more information view our Privacy Policy.

Before Your Arrival

  • We require a two-night minimum stay year-round, except during certain times of the year when a three-night stay is required.
  • To confirm your reservation, a one-night’s deposit at the time of booking is required. Final payment will be charged to the credit card on file 48 hours prior to arrival.
  • Lodging rates are subject to a combined sales and lodging tax of 11% (6% MD and 5% Lodging).
  • 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 quoted for two guests and vary according to the day of the week and the season.
  • Please note that gratuities are solely at the Guest’s discretion and may easily be added to you folio upon departure.

Check-In Policies and Arrival Information

  • Check-In time is from 3 p.m. to  7 p.m. in the Summer months and 3 p.m. to 6 p.m. in Wintertime.
  • Should you require an arrival time later than 7 p.m., please let us know in advance.
  • Upon your arrival, we will gladly provide you with a tour of the Manor.
  • We would be delighted to recommend a number of local restaurants for your dinner and if you wish, to make any reservations for you.
  • Afternoon refreshments will be available.

Check-Out Policies

  • Check-Out time is any time prior to 11 a.m. on the expected day of departure.
  • All balances must be settled at the time of departure.

Cancellation Policy

  • All lodging reservations, including group bookings, require a 50% deposit at the time of booking.
  • Your deposit less a $50 cancellation/change fee per room will be returned for cancellations made 30 days or more prior to the scheduled arrival date.
  • Guests who shorten their stay within 30 days of arrival remain liable for all charges based on the reserved rate for all cancelled nights. All early departures and no shows will be charged at the reserved rate for each unused room night.
  • For Holidays, Special Event Weekends including Tea Party Weekend, Down Rigging Weekend, Washington College Graduation Weekend, Washington College Parents Weekend and Multiple Room Bookings the deposit less $50 per unit will be refunded if cancelled 60 days prior to scheduled arrival. All money is due if not cancelled 60 days prior to scheduled arrival.
  • The Group or Event Cancellation policy is contracted separately. If you are concerned about an unexpected emergency preventing your arrival, we recommend trip insurance, for instance Travelinsurance.com or Allianz Travel Insurance.

Accessibility Policy

Great Oak Manor is committed to facilitating the accessibility and usability of this website for all people with disabilities. We will continue to implement the relevant portions of the World Wide Web Consortium’s Web Content Accessibility Guidelines 2.0 Level AA (WCAG 2.0 AA) or such other standards as required by the Americans with Disabilities Act (ADA). On a periodic basis, our website will be tested with assistive technology.

We work to ensure every guest who wishes to visit can do so regardless of their physical abilities. Among the ways we comply with ADA:

  • We ensure that individuals with disabilities can make reservations during the same hours and in the same manner as individuals without disabilities.
  • We have identified and described accessible features and inaccessible features in detail.
  • We ensure that accessible guest rooms are held for use by individuals with disabilities until all other guest rooms of that type have been rented.
  • We guarantee that a specific accessible guest room, once reserved, is held for the reserving guest. We make reasonable efforts with third-party reservation systems to make accessible rooms available through at least some of these services and they must provide these third-party services with information concerning the accessible features of the Manor and our accessible rooms.
  • Guests with legitimate service animals as defined in the ADA will be provided reasonable access to specific areas of the Manor.

Accessible Accommodations and Features:

  • Our Sterling Suite is a first-floor, accessible suite which offers a king bedroom and a large sitting room. The bathroom provides shower-only with assistive hand grips in the shower and by the toilet.
  • The Sterling Suite is closest to the parking area and also offers loading and unloading at its exterior door.
  • Common areas, dining rooms, and reception areas are wheelchair accessible.

If you require other items please inform us prior to your stay, and we will be happy to work with you to assure a pleasant and comfortable stay.

Please be aware that our efforts are ongoing. Please email us at info@greatoakmd.com or telephone 800-504-3098 with questions or concerns regarding ADA accessibility, including issues accessing the website or with questions regarding the accessibility and personal needs of the various suites and cottages.