The Eastern Shore Travel Guide

28 Hotels

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28 Hotels

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1

Brampton Bed & Breakfast Inn

$$$$ | Chestertown 25227 Chestertown Rd.

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

B&B/Inn


2

Combsberry

$$$$ | 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

B&B/Inn


3

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

Hotel


4

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

Hotel

5

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

B&B/Inn


6

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


7

Imperial Hotel

$$$ | Chestertown 208 High St.

This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today... Read More

B&B/Inn


8

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

9

Park Place

$$$Ocean City

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

Family


10

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


11

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


12

The Oaks, a Country Inn

$$$ | Royal Oak 25876 Royal Oak Rd.

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

B&B/Inn

13

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

B&B/Inn


14

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

B&B/Inn


15

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

B&B/Inn


16

Five Gables Inn & Spa

$$ | St. Michaels 209 N. Talbot St.

Three circa-1860 houses have been turned into an elegant and comfortable getaway. All rooms have a private por... Read More

B&B/Inn

17

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

B&B/Inn


18

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


19

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

B&B/Inn


20

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

B&B/Inn

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