Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century county-style estate rests on the waterfront of the Chesapeake Bay. With 12 questrooms, Great Oak offers the finest in a luxury Inn. Enjoy the most beautiful sunsets on the Eastern Shore from our private beach or our vast 12 acres of manicured lawns. We are members of the Select Registry Distinguished Inns.The Inn was featured on The Today Show with travel editor Peter Greenberg, and also featured in the February 2004 issue of Southern Living Magazine; in The Washingtonian "Dream Weekends", April 2003; in Baltimore ...
We just returned from a truely memorable weekend at Great Oak Manor Inn. From the moment we arrived and were met by Cassandra and John, we felt both special and like we had known them for years. The Great Oak Manor provides a sophisticated yet relaxed atmosphere that would appeal to nearly every taste. Being located on the water with spectacular Chesapeake Bay views, creates a most romantic setting which is only magnified by the tasteful interior decor and imaculate grounds. We were able to participate in a special, gourmet dinner, catered by a local Culinary Institute of America-trained chef. The evening made us feel like we had stepped back in time to a more genteel era, perhaps during the Guilded Age, where an evening would consist of live chamber music, fabulous food, and stimulating conversation. We were treated to live piano music from a virtuoso pianist while we enjoyed hors d'oeuvres and wine. Then we moved to the dining room where we were served a lavish dinner with wines specifically selected to pair with each course. After dinner we adjourned to the library for coffee or tea and great conversation with our fellow guests. The Innkeepers, Cassandra and John, acted as host and hostess throughout the evening and, given their warm, outgoing personalities, made the entire affair very special. We would heartily recommend the Great Oak Manor Inn to couples seeking a romantic getaway for a long weekend or for families gathering to celebrate a special event such as an anniversary or reunion. The breakfasts were sublime and included fresh, home baked muffins (we enjoyed banana/pineapple and pumpkin) along with never-ending platers of fresh fruit and yummy French toast with local sausage on one day and an egg and cheese dish on the other day. All in all, we would both return to the inn in a heart beat and have already recommended it to our friends.
Our two night stay at the Great Oak Manor was truly remarkable. The majestic inn sits right on the Chesapeake Bay with the most incredible views. The innkeepers were friendly, attentive and catered to our every need.
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