3 Best Hotels in The Eastern Shore, Maryland

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 miles south of downtown Chestertown, this mid-19th-century inn, known for its gracious hospitality, still resembles the plantation house it once was. The brick building's entrance has a 3½-story walnut-and-ash staircase, pine floors, and plaster ceiling medallions. All of the spacious, well-appointed guest rooms have working fireplaces (but only lit October through April), and five have hot tubs. Classic movies, available from the innkeepers' private collection, can be viewed in the library, which also has an extensive supply of books. Rates include a full country breakfast and afternoon tea with homemade pastries.

This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias and willows on the banks of Island Creek, a few minutes' drive from Oxford. Inside are five arched fireplaces, floral chintz fabrics, and polished wood floors. All the rooms and suites of this luxurious B&B have water views and are furnished with English manor–style antiques, including four-poster and canopy beds. Some also have hot tubs and working fireplaces; the two-bedroom carriage house has a kitchen.

On 25 acres beside the Miles River, this luxury inn—operated by the world-renowned Orient Express Hotels group—employs a nautical theme throughout to elegant effect. Each unique guest room has elegant appointments; amenities include heated towel racks, fresh flowers in all rooms, and afternoon tea. Above all, staying here means impeccable service. Dining at the inn's restaurant with its exquisite cuisine and stellar wine selection is an event. The signature crab spring roll with pink grapefruit, avocado, and toasted almonds, and the lamb shank glazed with honey and tarragon are both exquisite.