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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, beautifully appointed guest rooms, and 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.
4.8 on September 28, 2016
Our wedding in September 2016 was absolutely incredible and Great Oak Manor was the star of the show (besides us of course). Spending the weekend and having a place where our family and closest friends could stay with us was invaluable. The house is spectacular and fits perfectly with the beautiful grounds. It was fun deciding which of our relatives and friends would stay in each of Great Oak's large and welcoming rooms. Our ceremony was by the water, complete with bay views and a nice sunset. The back yard was a great setting for our cocktail hour and the side yard was prefect for our seated dinner and dancing. The staff couldn't have been more helpful all throughout the process, and especially during the weekend. A huge thanks to Great Oak and the team for a truly unforgettable wedding for us and all our guests!!
5 on June 18, 2016
Outstanding in all categories. The breakfasts are a delight, and full of surprises. It is remote enough to be out of the beaten path, but close enough to Chestertown and Rock Hall to enjoy equally outstanding dinners. There is a friendly and helpful staff if you should need anything. The rooms are of equally high standards. It would be difficult to find a better setting, with grounds on the Chesapeake Bay for relaxing and watching the sunsets over the bay. Highly recommended. Gene Larson
5 on November 19, 2015
Beautiful property, great service, fantastic views of the Chesapeake Bay. We are already planning our next visit. H. Sheneman
3.8 on October 08, 2015
The staff and Innkeepers were lovely and very helpful. Everything was just as stated on the website.
5 on August 24, 2015
Been to the manor twice and was best ambiance and environment I have ever experienced! Recommend you stay there it will set the standard you should expect from any provider in the industry!
4.6 on August 12, 2015
Everything was great! The staff was very courteous and helpful. All food preparations were unique, well prepared and presented. Love the old charm and country feel. Wonderful weekend getaway, looking forward to our next stay during the week.
5 on August 05, 2015
What an incredibly restful place, and so close to Washington, D.C. We stayed in the Roese Room, and the pet-friendly policy allowed us to bring Lucy. The staff were great. We are telling all our friends about The Great Oak !
5 on June 16, 2015
My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff, rooms. Favorite place on earth to paint.
4.6 on May 30, 2015
A wonderful stay at Great Oak Manor! Beautiful guest rooms, with new comfortable bedding. Lovely new wallpapers and paints. Helpful staff. Tasty breakfasts. Gorgeous sunsets. Great water views. Spacious grounds, terrific for strolling along the shore. Close to historically, architecturally interesting Chestertown. Charming!! Barbara Thompson
5 on April 08, 2015
I just returned from a wonderful two stay at the Great Oak Manor Bed and Breakfast. It was so relaxing! The view and sunset was spectacular! The new owners have up dated in and around the Manor. The one improvement was new bedding and linens.The Innkeeper was very friendly and happy to satisfy your every request. She served a fabulous breakfast and dinner. You feel like a special guest. Eileen Kuhn
Beautiful second floor, waterview room with sweeping views of the Bay. Fireplace and bed that looks right out to the water, our most popular room. Rise to breathtaking views of the Chesapeake Bay from a king-size bed that begs you to stay under the covers for a moment longer. Bright and airy, the Marmaduke features rich floral hues and is perfect for just gazing out at the view. With a cozy fireplace, walk-in closet and sumptuous bath, this luxury guest room is as lovely as the first land owner for which it is named. Being on the corner of the house affords the room ample space and natural lighting, also making this room perfect to act as our bridal/honeymoon suite for couples hosting their wedding at Great Oak Manor, or sharing a romantic getaway together. The Marmaduke has its own heating/cooling.
Marina, Chesapeake Bay waterfront, Countryside, Oceanfront, Small town
Baltimore, MD (BWI-Baltimore Washington) 65 miles
10568 Cliff Rd. Chestertown, MD. 21620 Visit Web Site for printable directions from the North and the South.
Antique Shopping, Art Galleries, Beach, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Sunset Cruises, Nature Trails, Sporting Clays, 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
Other, Historic Inn
Coffee/Tea facilities, Computer, Conference Rooms, Copier, Fridge, Library, Microwave, Piano, Private entrance, Satellite/Cable TV, Videos, Washer/dryer, Wedding Facilities, Wet bar , Golf, Tennis, Conceirge Services, Bicycles, Room safes
Air conditioning, Alarm clock, Amenities Basket, Bath robes, Board games, CD player, Ceiling fans, DVD Player, Desk, Fireplace, Hairdryer, Ironing Board, Radio, TV, Telephone, VCR, Wi-Fi, Wired internet
Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Fishing, Golfing, Hiking trails, Horseback riding, Horseshoes, Kayaking, Sailing, Shopping, Sight-seeing, Swimming, Tennis courts, Tennis racket rental, Water sports
Scott and Kaylin come to us from Philadelphia where they spent the last seven years experiencing the city of brotherly love. Scott has a background in hospitality and has managed hotels and restaurants in New York and Philadelphia. Kaylin has design, marketing and sales experience and has worked for various promotional marketing companies. As a couple and with their dog Molly of course they look forward to their new home in Chestertown and experiencing what the Eastern Shore has to offer. It is
Full buffet with hot entree
Low fat , Restrictive , Vegetarian Inquire upon booking
Farm to Table Modern
We strive to embrace using the freshest ingredients possible at Great Oak Manor. Our Innkeepers are hoping to continually expand the menu options for our breakfast tables to include ingredients from our own little garden and from local farms.They're also looking at creating a more modern approach to dishes.