Our waterfront Eastern Shore bed and breakfast has 12 romantic rooms featuring their own unique decor with individual highlights such as a cozy fireplace, a spacious bath with skylight, inviting French doors leading to the garden, or a rich red bathroom. Check out each room for their individual styles and rates.

Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay in Chestertown, Maryland, we offer a place to dream. Make yourself comfortable as you rest amongst the softest sheets on comfortable beds. Every morning is not only met with stunning views of the Chesapeake Bay, but also a full breakfast with seasonal fresh fruit, homemade baked goods, cold cereal, and a hot entrée.

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

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

Russell

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

Sterling

  • King bed
  • First floor
  • Private bath
  • Two room suite
  • Private entrance
  • Pet friendly

Caulk

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

Tylden

  • King bed
  • Second floor
  • Private bath
  • 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
Room Image Room Guests Bed Bath Features Book Room
Hynson Room bed and reading chair at our Chestertown B&B Hynson Two King Tub/shower combo Third floor, bay views Check Rates
Ringgold Room bed, reading chair, and desk at our Chestertown bed and breakfast Ringgold Two King Tub/shower combo Third floor, sunrise views Check Rates
Geddes-Piper Room offers exceptional weekend getaways from DC Geddes-Piper Two King Tub/shower combo Third floor, bay views, interior balcony Check Rates
Hodges Room bed and seating area at our bed and breakfast in Chestertown, MD Hodges Two King Tub/shower combo Second floor, sunrise views, fireplace Check Rates
Roese Room offers exceptional eastern shore getaways Roese Three King Tub/shower combo Second floor, sunrise views, electric fireplace, pet friendly Check Rates
Russell Suite bed and seating area with fireplace at our Chestertown, MD B&B Russell Four King Tub/shower combo Third floor, sunrise and bay views, fireplace Check Rates
Sterling Suite is one of the best places to stay in Chestertown, MD Sterling Four King Walk-in shower First floor, sunrise views, private entrance, sofa bed, pet friendly Check Rates
The Caulk Room offers incredible Eastern Shore romantic getaways Caulk Two King Tub/shower combo Second floor, bay views, balcony, pet friendly Check Rates
Tylden Room bed and seating area at our Eastern Shore B&B Tylden Two King Walk-in shower Second floor, bay views, balcony Check Rates
Wickes Room bed at our Eastern Shore Maryland bed and breakfast Wickes Two King Tub/shower combo Second floor, sunrise views, fireplace Check Rates
D'Oench Room offers exceptional Chestertown, MD lodging D’Oench Two King Tub/shower combo Second floor, bay views, fireplace Check Rates
Marmaduke Room offers the ultimate romantic getaways near DC Marmaduke Two King Tub/shower combo Second floor, bay views, fireplace Check Rates
Our Eastern Shore vacation rental dining and living room The Carriage House Six King & Queen Walk-in shower & claw foot tub Bay views, kitchen, double & single sleeper sofa Check Rates

Crusier Bicycles in our front lawn

Stay in Luxury on the Chesapeake Bay

At Great Oak Manor, our inn on Maryland’s Eastern Shore, we invite you to take full advantage of our luxurious accommodations. Enjoy your full breakfast in the Bay View Dining Room. Explore the books in the Library. Relax in the Sunroom and drink a cup of tea or coffee, always available 24 hours a day. Indulge daily in a sweet and savory afternoon snack, and nap in the hammocks or Adirondack chairs on the bluff. When you return from dinner, look forward to the complimentary Port and Sherry in the Music Room. Every Friday enjoy Manager’s Wine & Cheese Hour.

In Suite we Offer:

  • Private bathrooms with complimentary shampoo, conditioner and body wash and Turkish towel linens
  • Hair dryers
  • Flat screen, high definition televisions
  • DIRECTV with HBO
  • Fiber Optic Wi-Fi
  • Comphy bed linens
  • Robes
  • 6 guest rooms have fireplaces
    (fireplaces are operational from November 1 – April 1)

Amenities for Outside:

  • Cruiser bicycles
  • Kayaks, canoe, and paddle boards
  • Waterside firepit
  • Patio firepit
  • Private Chesapeake Bay beach access
  • 2 Tesla charging stations
  • Cornhole
  • Binoculars for bird watching
  • Use of amenities at the marina next door:
    • Pool
    • Fitness room
    • 9-Hole golf course (bring your own gear)

General Information and Reservation Policies

Please be sure to read the fine print for our Eastern Shore bed and breakfast. If you have any questions, call us at 410-778-5943 and we will gladly explain.

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 deposit upon booking.
  • A combined sales and lodging tax of 11% (6% MD and 5% Lodging) will be in addition to our nightly 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.

Check-In Policies and Arrival Information

  • Check-In times are from 3pm – 7pm in Summer and 3pm – 6pm in Winter.
  • 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 11am. 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

  • Your deposit minus a $35 cancellation/refund fee will be returned up to 30 days prior to the scheduled arrival date for a single room booking. All money is due if not cancelled 30 days prior to scheduled arrival. We will attempt to move the reservation to a future date in the same calendar year if cancelled prior to 14 days from scheduled arrival.
  • For Holidays, Special Event Weekends including Tea Party Weekend, Downrigging Weekend, Washington College Graduation Weekend, Washington College Parents Weekend and Multiple Room Bookings the deposit minus $35 per room will be refunded if cancelled 60 days prior to scheduled arrival. All money is due if not cancelled 60 days prior to scheduled arrival. We will attempt to move the reservation to a future date in the same calendar year if cancelled prior to 30 days from scheduled arrival.
  • Event contracts have their own cancellation policy written into the contract. Above policies do not apply.
  • If you are concerned about an unexpected emergency preventing your arrival, we recommend trip insurance such as https://www.insuremytrip.com or https://www.travelinsurance.com
  • No refunds for early departure.

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 Wi-Fi access, DirecTV and flatscreen TV’s, private baths, and heating/air-conditioning.
  • Please view our Pet Policies.
  • For more information view our Privacy Policy.