Great Oak Manor
10568 Cliff RoadChestertown, MD 21620
Toll-free 1-800-504-3098
Phone 1-410-778-5943
EmailContact by Email info@greatoakmd.com
Website http://www.greatoakmd.com
F. Scott Fitzgerald wrote of blue lawns and country houses such is Great Oak Manor. From the estate's walled garden bordered by 65-year old boxwoods and its circular drive on the estate side, to its magnificent view of the Chesapeake Bay and private beach on the water side, this country estate provides the appropriate setting for a relaxing getaway and a weekend of romance. Guest and public rooms are spacious, beautifully furnished and comfortable. A true Manor House with fine details, beautiful furnishings, Orientals, and an 850- volume library to browse, high speed WIFI access, plus 1,200 ft. of waterfront lawn on The Cheasepeake Bay, and the most beautiful sunsets on the Eastern Shore of Maryland.
Each guest will receive a lovely hot breakfast in the dining room overlooking the water. Join us at the waterfront inn on the Chesapeake.

$200-299, $300+
- Cash
- Check
- Visa
- MC
- Discover
- Traveler's Cheques
- Gift Certificates
Weekends, Holidays
Yes
Over 12
12
Coastal, Waterfront, Waterview, Small Town/Village
Onsite, Business Hours
- Pool
- Free Onsite Parking
- Gardens on Property
- Business Center
Onsite
Smoke-Free, Outside Only
Yes
Inside
Wired, Wireless, Complimentary
Limited

Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay, we offer a place to dream. Make yourself comfortable as you take a look at each one of our guest rooms in this Chestertown, Maryland luxury waterfront inn. Rest amongst the softest sheets on comfortable beds topped with down featherbeds. A luxury robe awaits your arrival—as well as bottled sparkling water, a light snack, and the finest bath and shower amenities .
Every morning is not only met with stunning views of the Chesapeake, but also a hot breakfast buffet with seasonal fresh fruit, homemade muffins, cold cereal, and a hot entrée, such as French toast, quiches or egg strata, is always offered. Enjoy your breakfast in the dining room, amongst much silver and china, or take it out to the terrace for a better view of the bay.
The Marmaduke;
Rise to breathtaking views of the bay from a king-sized bed that begs you to stay under the covers for a moment longer. Bright and airy, the Marmaduke features rich floral hues and chairs perfect for reading or gazing at the view. With a cozy fireplace, walk-in closet and sumptuous bath with soaking tub, this luxury guest room is as lovely as the first land owner for which it is named.
- Non-Smoking Rooms
- Suites
Queen, King
Private
Limited
In-Room
- Air Conditioning
- Antique Furnishings
- Bathrobes
- Featherbeds
- Fireplaces
- Hairdryers
- Private Deck
- Telephones
- Alarm Clocks
- Ironing Boards
- Turndown Service
- Cable TV
- CD Players
- DVD/VCR
- Video Library

When you are a guest at the Inn, a full breakfast is served in the dining room from 8:30 to 9:30 a.m. Afternoon refreshments are served in the Chesapeake Room and evening port and sherry are served in the Music Room every evening. Fresh fruit is always available.
Yes
Full
Individual Tables
No
Breakfast
- Special Diets Accomodated
- Vegetarian Options
- Complimentary Beverages
- Afternoon Tea/Refreshments
- Complimentary Snacks
- Early Coffee/Tea

- Antique Shopping
- Art Galleries
- Beaches
- Biking
- Boating
- Canoeing/Kayaking
- Culinary Classes
- Fishing
- Garden Tours
- Golf
- Hiking/Nature Trails
- Historic Sites
- Horseback Riding
- Hunting
- Library
- Rivers/Lakes
- Shopping
- Tennis

Take the road less traveled for your next business meeting or corporate retreat. In other words, take Cliff Road all the way out to Great Oak Manor, our waterfront inn in Chestertown, Maryland. Inspiration doesn’t come from a stuffy meeting room with fluorescent lights. Original thought happens in a meeting space with brilliant views of the Chesapeake—where all your needs are taken care of, so you can get down to business. Team building, group bonding, budgets, board of directors retreats, sales meetings, department head coordination......if it requires getting people together to think, plan, creat, or just reguvinate. Great Oak Manor Inn is coveniently located on the Eastern Shore, just 2 hours by car from DC, Virginia, Pennsylvania and New Jersey.
IKEA..."My colleagues and I have not stopped talking about Great Oak Manor. It was exactly what we needed....we will be back" December 2007
- Business
- Family Reunion
- Social
3
2200
60
24
24
100
150
- Dedicated Conference Center
- Onsite Catering
Indoor, Outdoor
60
60
More about our meetings services

Throwing a bouquet or throwing a banquet? Black-tie or tie-dye? No matter what you’re planning, a wedding, corporate event or a reunion party, the shores of the Chesapeake are the perfect setting for your next event. With a select list of the area’s finest caterers and chefs, your gracious hosts will take every step to ensure your party is a memorable one.
- Ceremony
- Receptions
- Rehearsal Dinner
- Bridal Luncheon
- Indoor
- Outdoor
100-199
More about our weddings services






