The Eastern Shore Hotels

Outside of Cambridge's singular Hyatt Regency and Ocean City's approximately 10,000 hotel rooms—the great majority of accommodations throughout this region a... Read More

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1. Brampton Bed & Breakfast Inn

$$$ | 25227 Chestertown Rd., Rte. 20 W, Chestertown, Maryland, 21620-3944, United States

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 mi south of downtown Chestertown,... Read More

2. Combsberry

$$$ | 4837 Evergreen Rd., Oxford, Maryland, 21654-1450, United States

This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias an... Read More

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3. Great Oak Manor

$$$ | 10568 Cliff Rd., Chestertown, Maryland, 21620-4115, United States

On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century... Read More

4. Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

$$$ | 100 Heron Blvd., Cambridge, Maryland, 21613-3420, United States

This 370-acre complex is the Eastern Shore's first full-service, year-round resort, and one that takes full ad... Read More

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5. Lighthouse Club Hotel

$$$ | 56th St. at Bay, Ocean City, Maryland, 21842, United States

This elegant boutique hotel is a Chesapeake Bay lighthouse lookalike of quiet luxury, just blocks from the bus... Read More

6. Park Place

$$$ | 2nd and 3rd Sts. at boardwalk, Ocean City, Maryland, 21842-4021, United States

Filling a need for more affordable, family- and child-friendly accommodations, this small, multistory hotel on... Read More

7. The Inn at Osprey Point

$$$ | 20786 Rock Hall Ave., Rock Hall, Maryland, 21661-1405, United States

On 30 lush acres along Swan Creek, this stately Colonial-era building welcomes guests with brick fireplaces an... Read More

8. The Lankford Hotel & Apartments

$$$ | 8th St. at boardwalk, Ocean City, Maryland, 21842-0420, United States

Opened in 1924, the Lankford is still owned by the family of the original owners. Many combinations of rooms i... Read More

9. Victoriana Inn

$$$ | 205 Cherry St., St. Michaels, Maryland, 21663, United States

Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War ar... Read More

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