The Eastern Shore Travel Guide
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28 Hotels

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28 Hotels

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Inn at Perry Cabin

$$$$ | 308 Watkins La., St. Michaels, Maryland, 21663-2114, United States

On 25 acres beside the Miles River, this luxury inn—operated by the world-renowned Orient Express Hotels group... Read More


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




$$$ | 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



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



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


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


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



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


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


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



Bartlett Pear Inn

$$ | 28 S. Harrison St., Easton, Maryland, 21601, United States

Natives Jordan and Alice Lloyd returned to their hometown and bought a 220-year-old home (the former Inn at Ea... Read More



Elk Forge B&B Inn and Retreat

$$ | 807 Elk Mills Rd., Elk Mills, Maryland, 21920-2207, United States

A 20-minute drive from North East, Elk Forge is nestled among 5 acres of woods and gardens along Big Elk Creek... Read More



Lodgecliffe on the Choptank

$$ | 103 Choptank Terr., Cambridge, Maryland, 21613-1115, United States

Located on a rise overlooking the river, this elegant turn-of-the-20th-century country home was the first bed-... Read More



River House Inn

$$ | 201 E. Market St., Snow Hill, Maryland, 21863-2000, United States

With its welcoming front porch, this Victorian home and its adjacent cottages are on two lovely acres on the b... Read More


Robert Morris Inn

$$ | 314 N. Morris St., Oxford, Maryland, 21654-0040, United States

In the early 1700s this building on the banks of the Tred Avon River was crafted as a home by ships' carpenter... Read More


Ship Watch Inn

$$ | 401 1st St., Chesapeake City, Maryland, 21915-1227, United States

Three levels of broad decks mean that every room has a place from which to relax and watch all manner of water... Read More



The Oaks, a Country Inn

$$ | Rte. 329 at 329 Acorn La., Royal Oak, Maryland, 21662-0187, United States

Antebellum grace defines this 1748 mansion on 17 acres along the banks of Oak Creek, 3 mi from St. Michaels. T... Read More



Tilghman Island Inn

$$ | Coopertown Rd. (2nd right after Knapps Narrows Bridge), Tilghman Island, Maryland, 21671, United States

Warm and welcoming conviviality and casual elegance define this compact, modern resort overlooking the Chesape... Read More



White Swan Tavern

$$ | 231 High St., Chestertown, Maryland, 21620-1517, United States

Step back in time at this inn restored to its appearance circa 1790. Built as a home in 1733, it was a tavern,... Read More


Atlantic Hotel

$ | Boardwalk at Wicomico St., Ocean City, Maryland, 21842-0120, United States

Family-owned and -operated since 1923, the three-story, H-shaped frame hotel—Ocean City's oldest—is a replacem... Read More

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