The Eastern Shore Travel Guide

28 Hotels

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28 Hotels

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Inn at Perry Cabin

$$$$ | St. Michaels 308 Watkins La.

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

$$$ | Chestertown 25227 Chestertown Rd.

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




$$$ | Oxford 4837 Evergreen Rd.

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



Great Oak Manor

$$$ | Chestertown 10568 Cliff Rd.

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

$$$ | Cambridge 100 Heron Blvd.

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

$$$Ocean City

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


Park Place

$$$Ocean City

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



The Inn at Osprey Point

$$$ | Rock Hall 20786 Rock Hall Ave.

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


The Lankford Hotel & Apartments

$$$Ocean City

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


Victoriana Inn

$$$ | St. Michaels 205 Cherry St.

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

$$ | Easton 28 S. Harrison St.

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

$$ | Elk Mills 807 Elk Mills Rd.

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

$$ | Cambridge 103 Choptank Terr.

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

$$ | Snow Hill 201 E. Market St.

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

$$ | Oxford 314 N. Morris St.

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

$$ | Chesapeake City 401 1st St.

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

$$ | Royal Oak Rte. 329 at 329 Acorn La.

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

$$Tilghman Island

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



White Swan Tavern

$$ | Chestertown 231 High St.

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

$ | Berlin 2 N. Main St.

This fully restored 1895 inn blends the taste of grand living with modern conveniences. Spacious, hardwood-flo... Read More

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