One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay just outside of Chestertown in Maryland's Eastern Shore. With large common rooms and beautifully appointed guest rooms, comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.The Manor will meet your every need with 1,200 ft. of waterfront, a private beach and the most beautiful sunsets on the Eastern Shore.
Deluxe waterfront room with comfortable furniture in front of the fireplace, large bath, walk in closet, and sitting area. Enjoy the bay view from your King size feather top bed. The room is tastfully decorated with antigues,
Deluxe two room suite with garden and courtyard views, fireplace is in the livingroom with the TV, walk-in closets, King size feather top bed is in a large seperate bedroom. Large tiled bathroom with skylight.
Charming Estate view room with fireplace, sitting area filled with antiques,Queen size four poster bed, private bath, walk in closet
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.
Rekindle a romance in front of a roaring fireplace in a room that overlooks the grounds of our magnificent estate. Named for Captain Lambert Wickes, skipper of the 16-gun sloop that carried Benjamin Franklin to France, this room features a king-size bed, a walk-in closet, and a large, private bath. Crown molding and chair rails, built-in bookcases, reading chairs, and paintings of sailboats add just the right finishing touch.
With an Oriental Mural, think of it as Georgian meets Asian fusion. The king-size bed with feather topper is the perfect place to curl up and read a book as you gaze out at the bay. A small area outside the door is a great place to watch the sun set over the bay. Tylden bathroom features a stand alone shower in its private bath.
There’s something about this room that makes you feel right at home. Nestled away on the third floor, this intimate place boasts an interior balcony where you can watch the boats go by on the bay, and a fine collection of black and whites from photographer, Marion E. Warren. The Geddes-Piper room boasts a king-size bed and a private bath.
Named for Great Oak’s most notable gamer, the Russell Room boasts a plush lounge area, a large television, a fireplace, and a large bath. This majestic room has an old boy’s club feel with a softer side. Rich reds, plaids, and mahogany walls are downplayed by the oriental rugs, crisp linens, and Ralph Lauren curtains. Let the games begin.
Comfort knows no boundaries in the graceful Ringgold room, which possesses a king bed, a full bath, and cottage-style comfort. Blue gingham and French toile complement the white wainscoting and duvet. The Ringgold truly feels like your home by the sea—or in this case, the bay.
The water calls you out to your own small private deck, which overlooks the Chesapeake. Enjoy a cocktail on the deck bar stools as the sun sets over the bay. Named for the Caulk battlefield and the only battle fought on the Eastern Shore in the War of 1812, this room is filled with history. The private bath boasts walls the color of the sunsets, an inviting, rich red.
The Hynson possesses the charm of a French country cottage, with the comforts of an estate home in Provence. Look out a dormer window to find inspiring views of the water and the grounds of the estate. The Hynson also features a private bath.
Charming third floor rooms with king size beds, private baths and dormer windows. All of our rooms have a TV and telephone.
This lovely first floor suite has french doors from the bright sunny bedroom to the Inns courtyard garden. This is also our pet friendly room.The living room is where you can curl up with a good book on the sofa or watch TV. The private bathroom has a large walk in shower.
5 on May 15, 2013
Incredible view - fantastic manor - wonderful innkeeper! Incredible breakfasts! MY FAVORITE INN IN THE WORLD!!!! Time stopped for us. Bring a great book or catch up on your magazines as there are many chairs and some hammocks that say "sit, stay & enjoy!!!"
3.8 on August 19, 2012
My husband and I have been visiting Great Oak Manor for over 20 years. During that time the property has changes owners three times. It is always a pleasure to find that the lovely B&B stays as gracious and beautiful throught out the transitions. With beautiful rooms and friendly staff, rolling back lawns that meet the Chesapeake bay, hammocks and lounge chairs to sit in while one reads or watches the eagles and osprey fish, or puttering round Chestertown and near by Rock Haall, Great Oak Manor is a perfect get away, oh and yes, breakfast is yummy as well!
4.8 on June 24, 2012
We experienced a beautiful weekend stay at the Great Oak Manor! It was the perfect venue for a quiet yet fun celebration for our anniversary and my birthday! The rooms are gorgeous and the complimentary breakfast is delicious! A great place to just BE.
4.8 on June 03, 2012
Meticulously maintained, beautiful decor in a beautiful setting. Outstanding service as well. The property is off the beaten path but a short drive to historic towns and other attractions.
4.6 on May 27, 2012
My husband and I spent 3 nights at Great Oak Manor in May. We wanted a beautiful place on the water that was peaceful and quiet. And that is exactly what we had! The public spaces are elegant but comfortable. Breakfast was cooked to order every morning. We even saw a lovely sunset on the first evening. The staff was very friendly and extremely helpful. We will definitely go again!
4.8 on May 20, 2012
Stayed three nights with relaxation, friendly helpful staff and delicious breakfast. Definitely recommend.
5 on May 04, 2012
My wife and I stayed at the Manor in April 2012. Know what you are looking for: this is a somewhat remote, beautiful, serene gorgeous place. No miniature golf, no neon, no nonsense. But "Wow!" Just beautiful. On the Chesapeake Bay. With, incidently, beautiful Persian rugs.
5 on February 28, 2012
Although it was only for 1 night, it was the perfect stay. We were greeted when we drove up by Cassandra and Charlie (tail wagging) and I immediately felt at home. After a tour of their beautiful home, showing us where everything was. Our room was beautiful and after settling in were spoiled by a nice tray of cheeses and fruit before heading out to dinner. After a great meal in Chestertown, we came back to our room and enjoyed the fireplace in our room and quiet time. We awoke to a beautiful view outside our room of the river and enjoyed a wonderful breakfast with eggs and fresh blueberry muffins. Excellent service and hospitality. Thanks to all for making our short stay a memorable one!
4.0 on February 01, 2012
We love this place, in winter and summer both! It is so relaxing!
5 on November 13, 2011
Cassandra and John are terrific! We have stayed in their "home" many times and always look forward to our next visit. Their friendliness is genuine and Cassandra runs an awesome inn! Thanks! Beth W
Marina, Chesapeake Bay waterfront, Beachside, Countryside, Small town
Baltimore, MD (BWI-Baltimore Washington) 65 miles
Philadelphia International is also within 90 minutes. Detailed directions provided with confirmation.
Antique Shopping, Art Galleries, Beach, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Historic Washington College, Historic Churches, Chesapeake Bay, Wildlife Refuge, Maryland Scenic Highway Rt. 213, Bird Migration, Outlet Stores, Performing Theater, Picnic area, Religious Services, River
Historic Inn, Country Inn, Other
Computer, Conference Rooms, Copier, Fax Machine, Library, Piano, Private entrance, Satellite/Cable TV, Videos, Washer/dryer, Wedding Facilities, Wet bar , Golf, Indoor exercise pool, Tennis, conceirge services, Bicycles, Room safes
Air conditioning, Alarm clock, Amenities Basket, Bath robes, Board games, CD player, Ceiling fans, Coffee/Tea facilities, DVD Player, In-room internet, Desk, Fireplace, Fridge, Hairdryer, Internet Service, Ironing Board, Radio, TV, Telephone, Turndown Service, VCR, Wi-Fi
Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Fishing, Golfing, Hiking trails, Horseback riding, Horseshoes, Hunting, Kayaking, Nature Trails, Sporting Clays, Sunset Cruises, Sailing, Shopping, Sight-seeing, Swimming, Swimming pool, Tennis courts, Tennis racket rental, Water sports
Full buffet with hot entree
Low fat , Restrictive , Vegetarian , check our specials
Our Breakfast buffet has seasonal fresh fruit, homemade muffins and breads, cold cereal, yogurts and a hot entree'. Depending on the day, you may be served either French toast and sausage, crab quiche or quiche Lorraine, eggs and ham to order, your preference, or an egg strata.