Located on Maryland’s Eastern Shore, Chestertown is home to many 18th-century Georgian- and Federal-style homes, and the vernacular-style White Swan Tavern bed-and-breakfast. A 2023 renovation completed by the inn’s new owners combines the old-world charm of antique and reproduction furniture with modern amenities, including updated guest bathrooms with glass-enclosed showers.
The inn is a short walk to the town’s waterfront and Washington College (founded in 1782, it was the first college chartered in the sovereign United States), plus restaurants, art galleries, shops and a Saturday morning farmers market.
Each of the inn’s six period guest rooms and suites has a comfortable bed with luxury linens and decor that is a nod to the property’s history.
The spacious John Lovegrove Kitchen room—named for the 1730s shoemaker whose one-room dwelling was the lot’s first building—is a guest favorite for its rustic brick floor, open-beam ceiling, cozy seating and elegant bathroom.
While most small inns have guest rooms with a single king or queen bed, White Swan’s The Wilmer Room is ideal for a larger family or friends getaway, with two four-poster double beds and a sitting area with views of the heart of Chestertown.
Rates begin at $150 and include coffee and tea any time of day, plus a full hot breakfast to enjoy in the dining room, or on the shaded back patio or front porch.
White Swan Tavern, 231 High St., Chestertown, Maryland, 410-778-2300
