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Eastern Shore, Maryland and Surrounding Area - Bed and Breakfast Inns

For over 20 years, Pamela Lanier's Travel Guides have been the savvy travelers' key to great deals on quality, romantic Eastern Shore bed and breakfast lodging and country inns. Search our database of Eastern Shore B&B's and you'll find detailed listings, current rates, and special deals for bed and breakfasts in Eastern Shore, Maryland.


Amenities Matching:  

Business Services

A host of bed and breakfasts offer top-rate business services, including faxes, copiers, on-site administrative assistants, computer hook-ups and more. If you are traveling on business, or just need to stay plugged into the real world, a bed and breakfast is an excellent choice.



All Cambridge Maryland, Bed and Breakfasts City Guide | Map it
Mill Street Inn bed and breafast

Mill Street Inn

Cambridge, MD


Rooms: 3
With Private Bath: 3
Rates: 125.00- 225.00 USD
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Great getaways begin here, where the pineapple truly signifies welcome, and where visitors will experience Eastern Shore hospitality at its finest.


All Chesapeake City Maryland, Bed and Breakfasts Map it
Blue Max Inn bed and breafast

Blue Max Inn

Chesapeake City, MD


Rooms: 10
With Private Bath: 10
Rates: 100.00- 250.00 USD
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This elegant bed & breakfast is located in historic Chesapeake City, Maryland, along the shores of the famous Chesapeake and DE Canal. Built in 1854, The Blue Max Inn is a charming and romantic inn located in the heart of this historic town.

Ship Watch Inn bed and breafast

Ship Watch Inn

Chesapeake City, MD


Rooms: 10
With Private Bath: 10
Rates: 99.00- 245.00 USD
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A stunning waterfront view can be enjoyed from all 10 guest rooms which are beautifully appointed in simple, elegant decor. A private bath accompanies each room and 6 feature whirlpool tubs with shower.


All Chestertown Maryland, Bed and Breakfasts Map it
Great Oak Manor bed and breafast

Great Oak Manor

Chestertown, MD


Rooms: 11
With Private Bath: 11
Rates: 165.00- 310.00 USD
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Come for a romantic getaway to Great Oak where the only honking comes from the geese, where the closest highway is the duck flyway, and where the only traffic you see from your room are the boaters sailing the water of the Chesapeake Bay Waterfront.

The Inn at Mitchell House bed and breafast

The Inn at Mitchell House

Chestertown, MD


Rooms: 7
With Private Bath: 7
Rates: 109.00- 239.00 USD
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Take a step back in time in this 18th-century manor house in a quiet, rural setting. It is located between Chestertown and Rock Hall. Enjoy gardens, ponds and the Chesapeake Bay, a mere 1/2 mile away. This is nature lovers' paradise.


All Easton Maryland, Bed and Breakfasts Map it
Bishop’s House B&B bed and breafast

Bishop’s House B&B

Easton, MD


Rooms: 5
With Private Bath: 5
Rates: 185.00- 195.00 USD
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Enjoy a memorable visit to MD's Eastern Shore. Romantically furnished, in-town, centrally located for visiting all points of interest. Victorian ambiance with 21st century comfort featuring working fireplaces, whirlpool tubs, WiFi & sumptuous breakfasts!


All Elkton Maryland, Bed and Breakfasts Map it
Elk Forge B&B bed and breafast

Elk Forge B&B

Elkton, MD


Rooms: 12
With Private Bath: 12
Rates: 89.00- 239.00 USD
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Nestled on five acres of beautiful woods and gardens along the Big Elk Creek. The area is rich in history and natural beauty and is just 3 miles from I-95, and minutes from Newark and Wilmington, Delaware. Philadelphia and Baltimore are only an hour away.


All Oxford Maryland, Bed and Breakfasts Map it
Sandaway - Waterfront Lodging bed and breafast

Sandaway - Waterfront Lodging

Oxford, MD


Rooms: 18
With Private Bath: 18
Rates: 149.00- 299.00 USD
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Chesapeake Bay Romantic Bed and Breakfast featuring waterfront rooms with porches, million dollar views, a private beach, and great sunsets. Just 7 miles to St. Michaels when you take the car ferry!


All Pocomoke City Maryland, Bed and Breakfasts Map it
Friendship Farm Bed & Breakfast bed and breafast

Friendship Farm Bed & Breakfast

Pocomoke City, MD


Rooms: 4
With Private Bath: 4
Rates: 135.00- 180.00 USD
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Welcome to Friendship Farm Bed and Breakfast. The inn sits on twelve acres on the banks of the beautiful Pocomoke River in Somerset County - "nature's masterpiece".


All Princess Anne Maryland, Bed and Breakfasts Map it
Somerset House B&B bed and breafast

Somerset House B&B

Princess Anne, MD


Rooms: 6
With Private Bath: 6
Rates: 160.00 USD
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Located in the Princess Anne Historic District on the Eastern Shore of Maryland. You will enjoy the elegant and historic home, the extensive gardens, and the luxury of your own large well-appointed room, with private bath.


All Rock Hall Maryland, Bed and Breakfasts Map it
Inn at Huntingfield Creek bed and breafast

Inn at Huntingfield Creek

Rock Hall, MD


Rooms: 8
With Private Bath: 8
Rates: 145.00- 265.00 USD
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Elegant & historic 70 acre farm-estate. Beautiful telescoping farmhouse architecture. Ideal for country weddings or retreats. Well-appointed, comfortable rooms with fine linens and excellent beds designed to pamper. 1100' waterfront & dock.

Old Gratitude House B&B bed and breafast

Old Gratitude House B&B

Rock Hall, MD


Rooms: 5
With Private Bath: 5
Rates: 159.00- 249.00 USD
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Sandy and Hank have created a relaxing, comfortable and elegant Bed & Breakfast that takes full advantage of the soothing water's edge while also offering access to a variety of activities that will keep you pleasantly busy.


All St. Michaels Maryland, Bed and Breakfasts City Guide | Map it
The Old Brick Inn bed and breafast

The Old Brick Inn

St. Michaels, MD


Rooms: 20
With Private Bath: 20
Rates: 135.00- 350.00 USD
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Located in the heart of St. Michaels, The Old Brick Inn is an elegant, historic (circa 1816) Inn, with the European charm of a boutique hotel. Offering the comfort and personalized service found in only the finest Bed and Breakfasts.

Five Gables Inn & Spa bed and breafast

Five Gables Inn & Spa

St. Michaels, MD


Rooms: 20
With Private Bath: 20
Rates: 150.00- 425.00 USD
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Rooms feature gas fireplaces, porches & whirlpools with bathrobes & Aveda amenities. Enjoy the heated indoor pool, steam room & sauna Massage, facials and body treatments in the spa by appointment.

Wades Point Inn on the Bay bed and breafast

Wades Point Inn on the Bay

St. Michaels, MD


Rooms: 26
With Private Bath: 26
Rates: 152.00- 260.00 USD
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Grand Georgian style home on edge of Chesapeake Bay. Two thousand feet of gently curving shoreline wrap the Inn's private grounds, giving spectacular views to its rooms. Weddings & special events.

Aida’s Victoriana Inn bed and breafast

Aida’s Victoriana Inn

St. Michaels, MD


Rooms: 7
With Private Bath: 7
Rates: 129.00- 369.00 USD
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Aida's Victoriana Inn is located on the historic St. Michaels harbor. Situated next to the Chesapeake Bay Maritime Museum, we are in walking distance to all attractions. The inn is just 2 blocks from the main street, yet removed from the bustle of town.


All Tilghman Island Maryland, Bed and Breakfasts Map it
Black Walnut Point Inn bed and breafast

Black Walnut Point Inn

Tilghman Island, MD


Rooms: 7
With Private Bath: 7
Rates: 120.00- 250.00 USD
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Located on 57 acres of a wildlife preserve on the southern tip of Tilghman Island, this inn with expansive waterfront views is a sanctuary. Watch the sun rise over the Choptank River and set over Chesapeake Bay and leave the cares of the world behind.

Lazyjack Inn on Dogwood Harbor bed and breafast

Lazyjack Inn on Dogwood Harbor

Tilghman Island, MD


Rooms: 4
With Private Bath: 4
Rates: 159.00- 289.00 USD
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Our c. 1855 waterfront home, located in the village of unspoiled Tilghman Island Maryland, is within walking distance to fine restaurants and shops. The Lazyjack Inn has earned a reputation as one of the Eastern Shore's finest getaway destinations.

Chesapeake Wood Duck Inn bed and breafast

Chesapeake Wood Duck Inn

Tilghman Island, MD


Rooms: 7
With Private Bath: 7
Rates: 139.00- 249.00 USD
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Enjoy Chesapeake Bay lodging on Tilghman Island. This romantic Bed and Breakfast getaway brims with historic charm & gracious hospitality. The Inn offers a pristine waterfront setting, gourmet cuisine, and a choice of six guestrooms & one cottage suite.



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