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Brampton Bed and Breakfast Inn

– Chestertown, MD

Bed&Breakfast.com Diamond Collection

Award Winning Chestertown Inn on 20 acres with unforgettable suites and scrumptious breakfasts!...more

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  • Rates:
    $199 - $419
    per night
  • Reviews
    20  
  • Rooms
    13
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Inn at 202 Dover

– Easton, MD

Welcome to the Inn at 202 Dover Voted Top 10 Romantic Inns In America 2011...more

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  • Rates:
    $275 - $475
    per night
  • Reviews
    27  
  • Rooms
    5
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Inn at Huntingfield Creek

– Rock Hall, MD

*Welcome to Inn at Huntingfield Creek. This elegant 70 acre farm estate is a charming setting for country weddings as well as an ideal venue for retreats, small meetings and business conferences. *Well-appointed, comfortable rooms offer fine linens, plush robes, down comforters and wonderful beds all designed to pamper our guests. *With 1100' of waterfront on Huntingfield Inlet the wildlife, sunsets and serenity abound. *Birders will appreciate our proximity to Eastern Neck Wildlife Refuge. Bicyclers and kayakers enjoy ideal conditions. Tourists fall in love with the charming, small-town ambience of Rock Hall with its quaint shops and great restaurants. *Inn at Huntingfield Creek is perfect for everyone who wants to enjoy the finest Eastern Shore hospitality, wonderful food and simple country bliss. *Family and pet-friendly Cottages and InnTowne House Apt....more

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  • Rates:
    $179 - $285
    per night
  • Reviews
    59  
  • Rooms
    8
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Chez Amis B&B Inn

– Annapolis, MD

Come share a day, weekend or week with us and enjoy the state capitol of Maryland and all it has to offer. Our 4 bedroom Bed & Breakfast is located in the heart of historic Annapolis, Maryland and is nearby the State Capitol, St. John's College, the waterfront, city dock, the Naval Academy, antique shops and fabulous dining and entertainment places all within walking distance. Find comfort and old fashioned relaxation at Chez Amis. Since each guest room has a private TV, the French country styled common area is designed for reading, conversation, and playing many games of your choice. Bananagrams and scrabble seem to be our guests’ favorite. Refreshments and homemade cookies are available throughout your stay so we understand if you ‘sneak downstairs’ for just one last cookie. The dining area is a wonderful piece of carpentry that was built by the previous in owner. It comfortably fits our guests but we also offer supplemental seating if you choose a more intimate table....more

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  • Rates:
    $170 - $250
    per night
  • Reviews
    3  
  • Rooms
    4
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Historic Kent Manor Inn

– Stevensville, MD

Waterfront and wonderful. Minutes From Annapolis . . . Miles From The Ordinary!...more

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  • Rates:
    $129 - $285
    per night
  • Reviews
    2  
  • Rooms
    24
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The Annapolis Inn

– Annapolis, MD

Elegance extraordinaire for the perfect getaway, vacation or business trip! Experience incomparable luxury, comfort and convenience. Exquisitely decorated historic landmark home of Thomas Jefferson's physician. Perfect historic district location. The living room and dining room are stately salons still crowned with their original ornate gulded rosette crown mouldings. Fireplaces, tapestries, paintings, sculptures and antique furnishing surround you and create a relaxing ambiance of luxury and comfort. Three magnificent rooms have been appointed to anticipte your comfort, lifestyle and privacy, creating an atmosphere of pampering elegance and spaciousness. ...more

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  • Rates:
    $259 - $479
    per night
  • Reviews
    1  
  • Rooms
    3
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Annapolitan Bed & Breakfast

– Annapolis, MD

Quaint, colonial architecture, unsurpassed hospitality and unforgettable experiences await......more

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  • Rates:
    $79 - $195
    per night
  • Reviews
    61  
  • Rooms
    5
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Miles River Guest House

– Easton, MD

Miles River Guest house is a 3 bedroom elegant private 1500 square foot guest house 100 feet from the magnificent Miles River. The house, rented only to one party at a time, has a large master suite with king size bed and private bath and many windows with great views, on the first floor are two bedrooms, one with a king size bed and a smaller bedroom with Queen size bed and bath and great view of the water, and great room (we call it the River Room) with leather sofas, mahogany bar, kitchen, HD flat screen TV, Juke Box (set to free play), gas logs fireplace, ipod stereo. The property has a swimming pool, dock, 2 person kayak and canoe, and is abundant with osprey, blue heron, eagles, swan in the summer and Canada geese in the fall and winter. The interior and deck areas have high speed wireless internet. Spa services and massages are available by the pool, on the dock or in the River Room. Click on the link to our website for a video tour of the guest house and related video in attractions menu....more

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  • Rates:
    $250 - $300
    per night
  • Reviews
    30  
  • Rooms
    3
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Five Gables Inn and Spa

– Saint Michaels, MD

Five Gables Inn and Spa is a haven for relaxation located in three restored properties in the heart of St. Michaels. The Inn features twelve rooms and eight suites, all of which include seasonal gas fireplaces and whirlpool tubs; some include a balcony or porch. Guests enjoy Aveda bath amenities, an indoor pool, sauna, and steam room. Our Aveda Concept Spa offers Therapeutic Massage, Facials, Hydrotherapy Tubs, Wraps, Scrubs, as well as Aveda retail products. Five Gables Inn also features an expanded continental breakfast, bicycles for guests' use, and four pet friendly rooms....more

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  • Rates:
    $175 - $425
    per night
  • Reviews
    15  
  • Rooms
    20
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Sandaway Waterfront Lodging

– Oxford, MD

Book this weekend - #1 TripAdvisor - Member of Select Registry Inns, Small Hotels...more

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  • Rates:
    $169 - $299
    per night
  • Reviews
    40  
  • Rooms
    18
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Academy Bed and Breakfast

– Annapolis, MD

In the heart of downtown Annapolis, moments from City Dock, dining and the Naval Academy...more

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  • Rates:
    $165 - $250
    per night
  • Reviews
    1  
  • Rooms
    4
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Scotlaur Inn

– Annapolis, MD

The Scotlaur Inn is an Old-fashioned Delight, set in the heart of historic Annapolis. The Scotlaur Inn is family owned and operated by Ted & Beth. Our ten beautifully decorated guest rooms offer the look and feel of the early 1900's. All of our rooms are private bath, TV, AC/Heat, hair dryers, and personal amenities. While staying at The Scotlaur Inn, you can enjoy strolling through the historic streets of Annapolis and visit the United States Naval Academy, the beautiful sites of the Annapolis city dock, the historic homes on the little quaint side streets. Every morning you can join in, in our restaurant when our staff and guests say the pledge to the flag of the United States of America. This has been a family tradition for many years....more

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  • Rates:
    $85 - $160
    per night
  • Reviews
    25  
  • Rooms
    10
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Flag House Inn

– Annapolis, MD

The perfect location with on-site parking, king or twin beds, private baths, comfortable seating, good lighting, and in-room cable TV. On the block connecting the historic waterfront and the U.S. Naval Academy in the National Historic District, Flag House Inn offers five guest rooms (including a two-room suite). Splendid interiors are filled with original naval and nautical art and memorabilia, fine paintings, antiques, and reproductions. The large front porch, flying the state or national flags of guests, greets you with swings and teak benches. Enjoy a large, hot breakfast before visiting Flag House’s beautiful and historic neighborhood....more

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  • Rates:
    $160 - $300
    per night
  • Reviews
    11  
  • Rooms
    5
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Gibson's Lodgings Bed & Breakfast

– Annapolis, MD

Location! Location! Location! Gibson's couldn't be any closer to the Dock & USNA! FREE PARKING...more

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  • Rates:
    $149 - $259
    per night
  • Reviews
    27  
  • Rooms
    20
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Wades Point Inn On The Bay

– McDaniel, MD

Spectacular wrap-around waterview with fabulous sunsets! Minutes from St. Michaels, this historic Inn and farm, offer a unique experience of timelessness, peace and beauty. 24 of the 26 rooms overlook Cheseapeake Bay. 120 Acres of fields, woodlands and ponds (with one-mile nature trail), a dock for fishing and crabbing and swimming or floating on rafts. Deer in the fields, bald eagles in the trees. Kayaks and bicycles available. Interesting shops and fine dining, the famed Chesapeake Bay Maritime Museum and other attractions are nearby....more

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  • Rates:
    $159 - $264
    per night
  • Reviews
    9  
  • Rooms
    26
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Gatehouse of Annapolis Bed and Breakfast

– Annapolis, MD

A bed & breakfast of distinction catering to the discerning traveler and business-person. Located in the heart of the Annapolis historic district, overlooking the US Naval Academy, a short walk from St. John's College, the State Capitol, and the City docks, The Gatehouse of Annapolis is an oasis for the connoisseur of travel. The Gatehouse of Annapolis offers superior hospitality and well-appointed accommodations for those who desire the highest level of personal service, elegant surroundings, unparalleled ambiance, and sumptuous cuisine prepared on the premises with the freshest ingredients available. ...more

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Hambleton Inn Bed and Breakfast

– Saint Michaels, MD

Nestled in the harbor and located right in the historic district of St. Michaels, the Hambleton Inn is within walking distance of antiques shops, art galleries, and perhaps the finest seafood restaurants in the world. Located in St. Michaels, Maryland, one of the great sailing capitals of the world, and the site of Michener's novel Chesapeake, the Hambleton Inn is a treasure of the bay. Guest rooms are spacious and appointed with antiques and oriental rugs. Gourmet breakfast is served every morning. Attention to details, personal service and friendly innkeepers all make your visit relaxed and simply wonderful. Just an hour from Baltimore Washington International Airport, the Hambleton Inn is easily accessible, yet a wonderful retreat, right on the water in historic St. Michaels, the Nantucket of the Chesapeake Bay....more

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  • Rates:
    $175 - $425
    per night
  • Reviews
    6  
  • Rooms
    8
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Black Walnut Point Bed & Breakfast Inn

– Tilghman, MD

Black Walnut Point Inn is located at the end of Tilghman Island on 57 acres of a waterfront wildlife sanctuary. Our own six-acre island at the end of the point, you can watch the sunrise over the Choptank River and set over the Chesapeake Bay. Both the 1840s house and private luxury cabins are open year-round, and every accommodation has endless water views and private baths. Enjoy the pool, hot tub, bird watching, fishing or just relaxing with a good book. If you enjoy nature or need a private retreat, come to the Black Walnut Point Inn - the secret place of peace....more

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Hot deal: 20% Off Weeknight Stays

  • expires Wednesday
  • Regular Rate: $200
  • Savings: 20%
  • Discount rate: $160

20% off all 2-night stays Sunday-Thursday, Labor Day-Memorial Day excluding holiday weekends. Reserve online or call us: 410-886-2452. Please contact the inn directly at +1-410-886-2452 to redeem this deal.

  • Rates:
    $125 - $325
    per night
  • Reviews
    35  
  • Rooms
    7
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Moonlight Bay Marina & Inn

– Rock Hall, MD

Moonlight Bay Marina hugs the shore of the beautiful Chesapeake Bay. Here, nature's beauty is as far as the eye can see. As you enjoy the park like setting, the bay breezes and the sound of the sea birds engulf you. Whether you are watching the ever changing scenes of the bay or meditating in the English Garden, all views are truly a painter's paradise. One of the highlight of the day is gathering to watch the spectacular sunset. Moonlight Bay Marina is steeped in history....more

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  • Rates:
    $149 - $190
    per night
  • Reviews
    5  
  • Rooms
    10
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Lazyjack Inn on Dogwood Harbor

– Tilghman, MD

From 1800's ceiling beams to complimentary DSL wireless access...more

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  • Rates:
    $166 - $289
    per night
  • Reviews
    61  
  • Rooms
    4
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The Taylor House

– Annapolis, MD

Located only minutes from the heart of Annapolis, The Taylor House offers pristine, spacious rooms....more

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  • Rates:
    $75 - $85
    per night
  • Reviews
    29  
  • Rooms
    3
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Annapolis Royal Folly

– Annapolis, MD

Within the heart of Historic Annapolis stands a timeless treasure: the Annapolis Royal Folly B&B. The Royal Folly, circa 1870, boasts 5 spacious suites, all private and seperate from each other and all with private bath, some with Jacuzzi and/or hot tub. Designed to be an oasis of comfort, Royal Folly coalesces 21st century conveniences with an atmosphere of casual elegance. With bright, spacious rooms, significant charm, and friendly environment, Royal Folly wants guests to feel both privileged and relaxed....more

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  • Rates:
    $195 - $395
    per night
  • Reviews
    3  
  • Rooms
    5
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Robert Morris Inn - Historic Restaurant with Rooms

– Oxford, MD

Arguably America's oldest Inn celebrates 300 years with new owner, celebrity Chef Mark Salter....more

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  • Rates:
    $145 - $240
    per night
  • Reviews
    29  
  • Rooms
    16
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Georgian House Bed and Breakfast

– Annapolis, MD

Located in the heart of Annapolis’ Historic District, enjoy an elegant step back in time...more

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  • Rates:
    $150 - $250
    per night
  • Reviews
    5  
  • Rooms
    4
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Laurel Grove Inn on the South River

– Annapolis, MD

Laurel Grove Inn is an 8,400 sqft. home located on 3 acres overlooking the South River in Annapolis....more

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  • Rates:
    $125 - $175
    per night
  • Reviews
    41  
  • Rooms
    5
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Victoria Gardens Inn

– Cambridge, MD

Built in 1890, Victoria Gardens is a tastefully restored landmark Victorian Heritage House. The beautifully landscaped property is alive with English gardens, centuries-old boxwoods and flowering perennials and trees. Located in an historic neighborhood and surrounded by unique houses of architectural signifigance, Victoria Gardens Inn looks out across the tranquil and wide Choptank River....more

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  • Rates:
    $190 - $190
    per night
  • Reviews
    4  
  • Rooms
    4
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Charles Inn

– Annapolis, MD

Come enjoy a bed and breakfast in the historc district of Annapolis, Maryland....more

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  • Rates:
    $149 - $279
    per night
  • Reviews
    16  
  • Rooms
    3
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Lodgecliffe on the Choptank

– Cambridge, MD

Cambridge's only waterfront bed and breakfast is waiting to welcome you!...more

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  • Rates:
    $180 - $200
    per night
  • Reviews
    132  
  • Rooms
    4
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Inn at Osprey Point

– Rock Hall, MD

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Hot deal: SAVE 20% ON TWO CONSECUTIVE WEEKDAY BOOKINGS

  • expires Wednesday
  • Regular Rate: $340
  • Savings: 20%
  • Discount rate: $272

Book two or more consecutive weekdays in the rooms "Alondra", "Shamrock", or "Cotton Blossom" and receive 20% off your entire stay. All other rooms are included with 20% off the regular rates. You must mention this ad to receive the discount. The rates above are for the two nights, not including taxes. The restaurant is open Wednesday through Sunday. You will receive a 10% discount on the food portion of your bill when dining in our restaurant. If there is a concert at the Mainstay, a local musical venue, we offer 2 free tickets to those performances (a $30-$40 value). Please mention this Hot Deal to get the discount. Please contact the inn directly at 14106392194 to redeem this deal.

  • Rates:
    $80 - $280
    per night
  • Reviews
    61  
  • Rooms
    15
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Reynolds Tavern

– Annapolis, MD

A beautifully restored Tavern, Reynolds reflects the working nature and the elegance of the 18th Century. It is the oldest tavern in Annapolis and one of the oldest in the U.S. We have 3 guestrooms all en-suite and luxuriously appointed, which offer a unique atmosphere just steps away from the Capital Building. Whatever your tastes the Tavern has something to offer you. Sly Fox Pub & Restaurant in the cellar gives you a flavor of what a pub was like over 250 years ago. We have casual dining and alfresco dining in the courtyard. Reynolds Tea Room has lunch, English afternoon tea and fine dining in the evening. We also offer special packages if you are celebrating a special occasion, or taking a well deserved "break". Ask us about our weekend packages that include Romantic Dinners, Champagne upon arrival - or even an in-room Massage!...more

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  • Rates:
    $220 - $295
    per night
  • Reviews
    17  
  • Rooms
    3
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Cambridge House B&B

– Cambridge, MD

Conveniently located within walking distance to the water, shops, restaurants, galleries and museums...more

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  • Rates:
    $150 - $225
    per night
  • Reviews
    40  
  • Rooms
    6
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Tarr House Bed and Breakfast

– Saint Michaels, MD

Enjoy the charm, elegance, and hospitality of one of the oldest restored homes in St. Michaels. Savor breathtaking views of St. Michaels Harbor, walk to fine restaurants, museums, and shops. A full breakfast is served! Come and enjoy Saint Michaels....you'll Love It....more

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Hot deal: Mid-Week Special

  • expires Wednesday
  • Regular Rate: $199
  • Savings: 25%
  • Discount rate: $150

Mid-Week Special $150.per evening which includes a full breakfast! Please contact the inn directly at +1-410-745-2175 to redeem this deal.

  • Rates:
    $169 - $225
    per night
  • Reviews
    5  
  • Rooms
    2
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Aida's Victoriana Inn

– Saint Michaels, MD

Open year round in the heart of town, gift certicates available. Off season rates call to enjoy....more

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  • Rates:
    $119 - $309
    per night
  • Reviews
    9  
  • Rooms
    7
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The Annapolis Farmhouse

– Annapolis, MD

swimming pool generous home cooked breakfasts golf in the area waterfront with pier two canoes and two kayaks waterview large front porch coffee stations in each room beautiful gardens wifi Annapolis is a very inviting town and the capital of Maryland. It has many historic homes, art galleries, museums, theaters, antique and craft shops, gardens, St Johns College and the U.S. Naval Academy. Take a tour of the Nations capital; visit Baltimore or Washington which are less than one hour away....more

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  • Rates:
    $106 - $133
    per night
  • Reviews
    2  
  • Rooms
    5
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The Bishop's House Bed and Breakfast

– Easton, MD

Victorian elegance with 21st Century conveniences featuring whirlpools, working fireplaces, individual climate control, (heat & A/C), off-street parking, complimentary wireless internet and sumptuous breakfasts! Accommodations are large rooms where lovingly created details such as antique furnishings are complimented with modern conveniences. Amenities include Shower Panels, Cable TV/DVD Player, CD Players, Clock Radios, Clock Radios for iPods, Ceiling Fans, Luxurious Sheets & Doeskin Guest Robes, Down Comforters, (in season), Hair Dryer, Lighted Make-up Mirror, Steam Iron & Ironing Board, Guest Refrigerator, Wine Cooler, Ice Maker, on site private off-street parking, secured overnight storage for bicycles, cycling tour maps of Talbot County, complimentary bicycles for guests use, wrap around porch & Courtyard with Fish Pond for rest and relaxation. Centrally located within three blocks of gourmet and casual restaurants, art galleries, museums, spas, antique & specialty shops, farmers' market, and an excellent location for visiting all points of interest in and around Maryland's Eastern Shore and the Delmarva Peninsula. Advanced Reservation Required. Two night minimum stay required for all guest rooms, year round. Inspected by & chartered member of the Maryland Bed and Breakfast Association. ...more

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  • Rates:
    $185 - $195
    per night
  • Reviews
    21  
  • Rooms
    5
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Bethel Bed and Breakfast, LCC

– Bethel, DE

Bethel Bed and Breakfast is a quaint Victorian home overlooking the scenic Broad Creek River in the ...more

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Meadow Gardens Bed and Breakfast

– Annapolis, MD

comfort of home, quiet, spacious grounds, water front, sumptuous home cooked breakfast, pet friendly...more

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  • Rates:
    $100 - $150
    per night
  • Reviews
    4  
  • Rooms
    3
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Schooner Woodwind

– Annapolis, MD

Woodwind's Boat & Breakfast includes a delightful two-hour sunset sail, overnight stay aboard the 74-foot, wooden Schooner Woodwind and a gourmet breakfast while overlooking the Annapolis Harbor. For $289 (for a couple) including all taxes, you can experience a unique, romantic, and unforgettable overnight stay. The way it works: Enjoy our terrific sunset sail and when we return to the dock, excellent restaurants are steps away for dinner (not included in price). Woodwind will be waiting for you dockside when you're ready to sleep or to socialize with other guests, or the captain and to relax on deck. Breakfast is served around 8:30 am, and checkout is at 9:30 am. Ask about our combo cruises with our special events. Available Saturday nights only from the first Saturday in May through end of September....more

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Mill Street Inn

– Cambridge, MD

Eastern Shore hospitality at its finest. Luxurious accommodations and gourmet fare...more

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  • Rates:
    $135 - $225
    per night
  • Reviews
    74  
  • Rooms
    3
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Great Oak Manor

– Chestertown, MD

One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay just outside of Chestertown in Maryland's Eastern Shore. With large common rooms and beautifully appointed guest rooms, comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.The Manor will meet your every need with 1,200 ft. of waterfront, a private beach and the most beautiful sunsets on the Eastern Shore....more

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  • Rates:
    $159 - $315
    per night
  • Reviews
    75  
  • Rooms
    12
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Simply Bed & Bread

– Chestertown, MD

Quietly tailored travel: 2 bright, spacious, allergy-friendly rooms in a cozy 1947 Cape Cod....more

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  • Rates:
    $119 - $149
    per night
  • Reviews
    1  
  • Rooms
    2
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Combsberry

– Oxford, MD

Combsberry is a beautiful English Country Manor located on Maryland's scenic Eastern Shore. The main house is an 18th century home set among mature magnolias and arching willows on the banks of Island Creek. Combsberry inevitably turns one's focus from history to romance. Escape to our B&B where all rooms, a private honeymoon/anniversary cottage and the carriage house provide splendid water views, distilling sunshine and warmth in any season. Relax in the king or queen sized pencil post beds, jacuzzis, fireplaces and English garden. Spend your days shopping and sightseeing in nearby St. Michaels and Easton or ride the oldest known privately operating ferry in historic Oxford....more

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  • Rates:
    $250 - $395
    per night
  • Reviews
    18  
  • Rooms
    6
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Peaches and Dreams Bed and Breakfast

– Cordova, MD

Quiet, peaceful country setting. Hot tub and inground pool. Hot, homemade breakfast....more

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  • Rates:
    $115 - $140
    per night
  • Reviews
    63  
  • Rooms
    3
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Ruffled Duck Inn

– Oxford, MD

The Ruffled Duck Inn is nestled in the historic district of the charming Eastern Shore Village of Oxford, Maryland. This completely renovated historic inn is the light hearted vision of yachtsmen Libby and Danny Cole. The blending of traditional and eclectic décor throughout the inn reflects their lives on the water as well as the rich history of the village that was once Maryland's largest port of call. ...more

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  • Rates:
    $140 - $165
    per night
  • Reviews
    6  
  • Rooms
    3
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Lodgecliffe on the ChoptankCambridge, MD

  • Nightly Rates $180 - $200
  • Reviews: 132
  • Rooms: 4
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"First timer"

"For a first time staying at a B&B it was just a wonderful and relaxing experience. The girls who take care of the house were wonderful."