Tucked away on a secluded cove on Maryland’s Eastern Shore, The Oaks Waterfront Hotel emerged from a $10 million-plus renovation in May 2023 that included the original circa-1748 building and other structures, as well as the grounds. Furnishings in warm whites and seaside blues impart a coastal vibe that carries through to the outdoors, thanks to new porches, patios, beautiful landscaping, firepits, and an old dock transformed into a pavilion for outdoor dining and watching movies under the stars.
While weekends are often booked with wedding guests, weekdays make for a peaceful getaway or even a remote work retreat—think laptop on a terrace overlooking the water, a midday stroll along the property’s winding brick path and an evening bath in an oversize soaking tub.
The 11 rooms and suites include king or queen beds, elegant tile bathrooms with heated floors, robes and Apple TV. Select rooms and all four of the cottages on the property have soaking tubs, private patios and water views. One of the cottages also includes a full kitchen and fireplace.
Dinner is currently available in The Oak Room on Wednesday and Thursday evenings with a menu featuring soups, salads, burgers, a veggie panini, and fish and chips made from Maryland blue catfish with malt vinegar aioli.
Alternately, a driver can transport guests, gratis, to shops and restaurants in nearby St. Michaels, Oxford and Easton. (Harley Peet, executive chef of Bas Rouge in Easton, was recently named “Best Chef: Mid-Atlantic” by the prestigious James Beard Foundation.)
Book the hotel’s 40-foot Hinckley Picnic Boat for a scenic fall sunset cruise or to explore an Eastern Shore town. Midweek rates begin at $389 per night and include a hot breakfast served in the dining room, plus complimentary use of bicycles, kayaks and paddleboards.
The Oaks Waterfront Hotel, 25876 Royal Oak Road, Easton, Maryland, 410-745-5053