The Eastern Shore Travel Guide

14 Hotels

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14 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 mi south of downtown Chestertown,... 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

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


4

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

B&B/Inn

5

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


6

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


7

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


8

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

9

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

B&B/Inn


10

Tilghman Island Inn

$$Tilghman Island

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

B&B/Inn


11

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


12

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

13

Inn of Silent Music

$ | Tylerton 2955 Tylerton Rd.

Located in a town that's separated by water from the other two villages on Smith Island, this remote English c... Read More

B&B/Inn


14

Kent Manor Inn

$ | Stevensville 500 Kent Manor Dr.

A summer hotel since 1898, this imposing antebellum manor house is on 226 acres of farmland along Thompson Cre... Read More

B&B/Inn

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