“Elegance on the Bay” is The Great Oak Manor, a historic 1938 Georgian-style building with all the modern touches on Maryland’s Chesapeake Bay.
We’re on the Eastern Shore of the Chesapeake Bay, just eight miles away from Chestertown MD. The Manor house and our beautiful grounds are perfect for a relaxing escape from the stresses and demands of your life back home.
The Great Oak Manor has twelve guest rooms, each with a private bathroom and king-sized bed. If you’re looking for a little privacy, our Carriage House offers a special retreat for two couples or a family looking for some peace and quiet.
Great Oak Manor also has our own small but private beach with a canoe, kayaks and stand-up paddle boats – take these out on the bay for a beautiful spring or summer day. We also have bicycles you can use tp cruise around our neighborhood.
The Manor and its property has a long history, dating back to the sixteen hundreds when Lord Baltimore deeded the land to Josias Fendall, a rebel against the crown. Fendall spent time in prison and lost his lands, so the property was transfered to Marmaduke Tylden. The Manor House itself was built by Russell D’Oench, heir to the W.R. Grace shipping firm. He hired a well-known Baltimore architect who won the state’s highest honor in architecture in 1940 for the amazing Georgian details incorporated in the house.
See the Great Oak Manor Expanded Listing on Purple Roofs Here