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||Two||King||Tub/shower combo||Third floor, bay views||Check Rates|
|Ringgold||Two||King||Tub/shower combo||Third floor, sunrise views||Check Rates|
|Geddes-Piper||Two||King||Tub/shower combo||Third floor, bay views, interior balcony||Check Rates|
|Hodges||Two||King||Tub/shower combo||Second floor, sunrise views, fireplace||Check Rates|
|Roese||Three||King||Tub/shower combo||Second floor, sunrise views, electric fireplace, pet friendly||Check Rates|
|Russell||Four||King||Tub/shower combo||Third floor, sunrise and bay views, fireplace||Check Rates|
|Sterling||Four||King||Walk-in shower||First floor, sunrise views, private entrance, sofa bed, pet friendly, accessible||Check Rates|
|Caulk||Two||King||Tub/shower combo||Second floor, bay views, balcony, pet friendly||Check Rates|
|Tylden||Two||King||Walk-in shower||Second floor, bay views, Juliet balcony||Check Rates|
|Wickes||Two||King||Tub/shower combo||Second floor, sunrise views, fireplace||Check Rates|
|D’Oench||Two||King||Tub/shower combo||Second floor, bay views, fireplace||Check Rates|
|Marmaduke||Two||King||Tub/shower combo||Second floor, bay views, fireplace||Check Rates|
|The Carriage House||Six||King & Queen||Walk-in shower & claw foot tub||Bay views, kitchen, double & single sleeper sofa||Check Rates|
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, outdoors in warm weather or delivered to your 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. Nap in the hammocks or Adirondack chairs on the bluff.
In Suite we Offer:
- Private bathrooms with complimentary shampoo, conditioner and body wash and Turkish towel linens
- Hair dryers
- Flat screen, high definition televisions
- Fiber Optic Wi-Fi
- Comphy bed linens
- 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
- Use of amenities at the marina next door:
- 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. Your final payment will be charged to the credit card on file 48 hours prior to arrival.
- 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.
- Early check-in is available for an additional $25 per hour.
- 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.
- Late check-out is available for an additional $25 per hour.
- 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.
- 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.
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 our bed and breakfast and guest rooms in detail to allow individuals with disabilities to determine whether our B&B meets their needs.
- 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 customer. 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 hotel and the accessible rooms.
- Guests with legitimate service animals as defined in the ADA will be provided access to all areas of the inn afforded to those without service animals
Accessible Accommodations and Features:
- Our Sterling Room is a first-floor, accessible suite which offers a king bedroom and a large sitting room. The bathroom is shower only with assistive hand grips in the shower and by the toilet.
- Our Sterling Room is closest to the parking area and also offers loading and unloading at its exterior door.
- Commons areas, dining areas, and check-in area 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. You may email us at email@example.com or call us 24/7 at 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.