About Great Oak Manor
Break out the Old Bay and crab legs because Great Oak Manor is the perfect destination for your Maryland vacation. A beautiful waterfront property located in Chestertown, this luxury bed and breakfast truly has it all. With the water so close, it’s a fantastic opportunity to get out there and get wet! Offering activities like boating, kayaking, fishing, and more, it’s a great way to truly take advantage of the area’s premium property. Nestled up to a private beach with plenty of room to stretch your legs, this picturesque property offers spacious room to explore and is just a taste of what the surrounding area has to offer. Relax in style with one of the Inn’s twelve rooms, dry off after a bath with soft Turkish towels, and warm up by the fireplace if the weather outside gets chilly. But of course, what would a trip to Maryland be without delectable food options to please the palate? Enjoy farm fresh eggs from Hens raised on the property and indulge in delicious homemade fresh baked granola. In addition, Great Oak is also pet-friendly! So, feel free to bring along your furry companion and watch the sunset over the water. The Manor truly has it all, an ideal way to spend a day in Chestertown.