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Step off the fast track to a place and time where the elegant living of yesteryear has been beautifully preserved. At Great Oak Manor in Chestertown, Maryland, the closest highway is the duck flyway and the only traffic you'll see from your charming Georgian-style guestroom are boats sailing on crystal waters. Within this magnificent country estate, recognized by American Historic Inns as among the Top Ten Most Romantic Inns, you'll luxuriate in that "get away from it all" feeling in a private and secluded locale on Chesapeake Bay.
Great Oak Manor
10568 Cliff Rd.
Chestertown, Maryland
21620
Nearest Airport: MTN
Immensely enjoyable: clean, spacious, knowledgeable staff, quite helpful. We would absolutely return for a longer stay.
ARCHIE G
We absolutely loved everything about our stay. Food was amazing, staff was amazing and the grounds and manor were amazing! A++
Heather Z
We enjoyed a beautiful vacation at Great Oak Manor! The home was gorgeous and our time here exceeded all of our expectations! My husband and I celebrated our 25 year anniversary and renewed our vows. From the moment we arrived, we felt welcome and were in awe of all the spaces throughout the home and outdoors. We enjoyed onsite massages and loved the extremely comfortable beds, high-end amenities, and breathtaking views. Everyone we came in contact with at Great Oak made sure we had everything we needed. The dining choices for breakfast and dinner were delicious and the service was exceptional. We also enjoyed the snacks, relaxing in the reading room, playing games in the conservatory, and smores by the fire pit. We could tell that every detail was thought of and we are grateful for all the ways everyone went above and beyond to ensure our 25th anniversary celebration and vow renewal was a memory my family and I will cherish. We absolutely made the perfect choice for our special celebration! This beautiful home and outstanding service is an experience our family won't ever forget. We look forward to coming back to Great Oak Manor for years to come and highly recommend to anyone seeking a relaxing and peaceful vacation.
Celeste H
We have been visiting Great Oak Manor for many years, attracted by the beautiful setting and proximity to the Chesapeake Bay. So we are fans of this venue, for sure. But I must say that over the past several years and with the current management and staff, this beautiful property has never been better! From the moment we were greeted by Corinne at the door, the staff went over and above to be sure that we were comfortable and felt at home. Corinne, Werten and, of course, Calin made us feel like old friends. And that same attention to detail and care is obvious in the house itself and how it is maintained and appointed. They have attained a level of quality that is rare and makes visitors anxious for their next visit. And that us how we left the manor the other day, anxious to return. Plans are in process to do just that. Thank you to Calin and the fine staff for another perfect visit! John & Sharon
JP1532
We really enjoyed our stay at the Manor. The manor was absolutely beautiful which was decorated nicely with stunning views especially sunset views. Many outside amenities of which we took advantage of such as hammock, fire pit, beach and just sitting on the adirondack chairs overlooking the bay. We had a room with the small balcony and it was nice to go outside and stand watching the boats. The breakfast's was absolutely delicious as well as their dinners were unbelievably good. The staff was so so very nice to us. Calin(manager) was so friendly and welcoming. When he saw us, he always stopped to talk to us especially my husband who is a talker. I highly recommend this place and my comments may not clearly articulate our experience. You will just have to check it out for yourself.
Angela S
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