Tucked away on 12 peaceful, bayside acres on the outskirts of Chestertown, Maryland, the elegant Great Oak Manor emerged from an extensive renovation in 2024 renewed and refreshed from the inside out—much the way guests feel after time spent in its serene setting.
Designed as a place to unplug and reconnect (with others, nature and yourself) the waterfront property is a respite from the digital grind. Have a drink by the fire in the cozy parlor, find a good read in the well-stocked library, or gaze with binoculars at the bird show outside the conservatory’s glass windows.
Give your phone a rest by tucking it into one of the “cell phone sleeping bags” in your room and head outdoors, where a gazebo amid the trees and Adirondack chairs lining the lawn provide a front-row seat to vibrant sunsets over the Chesapeake Bay.
Each of the manor’s luxurious 12 rooms and suites—six with bay views—features unique decor in a mix of soft whites and subtle greens and blues, a king or queen bed, Molton Brown bath amenities, bathrobes, a flat-screen TV, Wi-Fi and yoga mats. Some rooms also have a fireplace, desk or built-in bookshelves.
Another lodging option, the two-level, two-bedroom Carriage House Suite, feels like a home away from home with a full kitchen, leather sofa and chairs, fireplace, spacious bathroom with a soaking tub and walk-in shower, and numerous windows overlooking the bay.
Seasonally-inspired farm-to-table dinners designed by the manor’s chef feature ingredients sourced from area farms and suppliers, as well as Great Oak’s garden. Check the schedule for upcoming culinary event weekends. Previous themes have included “Love and Chocolate” and “An Appalachian Food Experience.” Additional dining options abound in Chestertown’s downtown.
Rates begin at $369 per night and include a gourmet breakfast, plus coffee, tea, sodas and snacks throughout the day. // Great Oak Manor, 10568 Cliff Road, Chestertown, Maryland, 410-778-5943