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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:  

Gift Shops

Many bed and breakfasts have the added benefit of an onsite gift shop where you can purchase last minute gifts and mementos for friends back home. Often carrying specialty items, gift baskets, wedding gifts, gift certificates, gift cards and unique collectibles, these shops provide an extra element of convenience for weary travelers.



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.


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.

Brampton B&B Inn bed and breafast

Brampton B&B Inn

Chestertown, MD


Rooms: 12
With Private Bath: 12
Rates: 179.00- 399.00 USD
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The award-winning Brampton Inn is a romantic Bed and Breakfast located on Maryland's eastern shore. 25 landscaped acres ideal for those seeking a luxurious and private escape. 1/2 mile outside the historic town of Chestertown.

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 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 Sherwood Maryland, Bed and Breakfasts Map it
Lowes Wharf Marina Inn bed and breafast

Lowes Wharf Marina Inn

Sherwood, MD


Rooms: 10
With Private Bath: 10
Rates: 95.00- 199.00 USD
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Country waterfront Inn located on the Chesapeake Bay proper. Featuring 10 guestrooms, all with waterviews, private bath, A/C-heat, coffee service, wireless internet, refrigerator and satellite TV. Marina. Beach access. Restaurant and Tiki Bar onsite.


All St. Michaels Maryland, Bed and Breakfasts City Guide | Map it
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.

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.


All Whitehaven Maryland, Bed and Breakfasts Map it
Whitehaven Hotel bed and breafast

Whitehaven Hotel

Whitehaven, MD


Rooms: 7
With Private Bath: 7
Rates: 110.00- 150.00 USD
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The Whitehaven Hotel is nestled on the shore of the Wicomico River, about 25 minutes outside Salisbury. One of the last of its kind, saved from the wrecking ball through cooperative efforts in 1995. Screened porch, working fireplaces.



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