Great Oak Manor Bed & Breakfast, Chestertown, Maryland, (MD)
Great Oak Manor Bed & Breakfast


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Great Oak Manor Bed & Breakfast

10568 Cliff Road
Chestertown MD 21620
(800) 504-3098
(410) 778-5943
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Innkeepers: Scott & Kaylin Benfield

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Great Oak Manor Bed & Breakfast a Chestertown, MD Bed & Breakfast

Come for a getaway to Great Oak Manor Bed & Breakfast in Chestertown, MD where the only honking comes from the geese, where the closest highway is the geese flyway and where the only traffic you see from your room are the boaters sailing the crystal water just 200 yards away.

Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that "get-a-way from it all" feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. We are situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and Philadelphia - all within a comfortable 1-1/2 hour driving distance.

Whether it's antiquing or shopping in Chestertown or Rock Hall, or dining at one of our many fine restaurants, there's much to do within minutes of the inn. On any day there's fishing, sailing, canoeing, kayaking, taking a shot at sporting clays, or cycling across the county along scenic byways. Next door at the landing you’ll find golfing, tennis, and birding... or just relax and watch the sunset from the Inn's own terrace. Great Oak is the place to come home to!
Activities & Attractions Go To Top
Antique Shops Antiquing Apple/Berry Picking Beach
Biking Bird Watching Boating Canoeing
Chesapeake Bay Christmas Tree Farm Classes and Courses Eastern Point Nature refuge
Fine Dining Fishing Golfing Hiking
Historic Chestertown Historical Sites Horseback Riding Hot Air Balloon
Hunting Kayaking Museum/Galleries National/State Parks
Ocean Outlet Stores Picnic Areas Private Beach
River Sailing Scrapbooking Shopping
Sight-seeing Swimming Tennis Theatre/ Concerts/ Performances
Washington College Water Sports Wildlife Preserves Winter Sports
(Amenities may not apply to all rooms - Please Inquire)
Go To Top
Air Conditioned Alarm Clock Amenities Basket Antiques
Bicycles Available Boat Docks (nearby) Business Travel Conference Facilities
Conference Room(s) Connecting Rooms Copier DVD
Desk Fax Fireplace in Common Area Fireplace in Room
Gardens (at inn) Guest Refrigerator Guest Telephone Hairdryer
Hammocks Handicapped Accessible (Limited) High Speed Data Port Ironing Board
King Bed Library Massage Available Meeting Facilities
Microwave Parking Piano Private Balcony
Private Baths Private beach and gazebo Queen Bed Swimming Pool
TV in Common Area TV in Room Telephone in Room Turndown Service
VCR Videos Wake Up Service Wireless Internet
Inn Known For Go To Top
Fall Foliage Gay/Lesbian Travel Girlfriends Getaways Gourmet Cuisine
Group Events National Register of Historic Places Receptions Romantic Escapes
Weddings/Vow Renewals
Forms of Payment Go To Top
Accepts Gift Gift Certificates
American Express Cash Checks
Discover Master Card Travelers Checks Visa
Discounts Go To Top
Corporate Discounts for groups Military Discounts Senior Citizen Discounts
Inspections/Associations Go To Top
Select Registry Distinguished Inns of America
Maryland Bed and Breakfast Association
Select Registry
Kent County Lodging Association
Maryland Bed and Breakfast Association
Languages Spoken By Innkeeper Go To Top
Meals Go To Top
Afternoon re-freshments Full Country Breakfast
Policies Go To Top
Check In Policy:
3 PM- 8 PM, please note that we cannot accommodate early check ins in your rooms.
Check Out Policy:
Cancellation Policy:
Cancellation must be made no later than 14 days prior to arrival. Cancellation made within 14 days will be charged a one night stay unless we are able to re-rent your room. There is a $25 re-booking fee for any cancellation once the reservation has been confirmed.
Children: Children ages 12+
All ages of children are welcome with whole house rentals.
Childcare: No
Deposit Policy:
A one night deposit is required.
Pets Welcome
One dog friendly room
Pets Living At Inn: Yes
2 cats that live in our private quarters,if you have allergies please let us know. We will try to be very respectful of this. New puppy golden retriever Charly on 7/17/08.
Smoking: Outside
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Great Oak Manor Bed & Breakfast a Chestertown, MD Bed & Breakfast

Maryland Bed and Breakfasts | Chestertown Bed and Breakfasts
Rate: $149-$315
Rooms: 12
Suites: 2
Handicap Accessible (limited)
Children ages 12+
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