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Showing 16-30 of 69 Resorts and Lodges

Brampton Bed & Breakfast Inn

Chestertown, Maryland, United States
$151

Finished in 1860 as the plantation house of the areas largest peach grower; Brampton retains today nearly all of its original details. They include the magnificent three and a half story central staircase, walnut windows and doors, original heart pine floors and plaster ceiling medallions. This thirty-five acre estate is conveniently located... more

Cambridge House Bed and Breakfast

Cambridge, Maryland, United States

The Inn at Mitchell House

Chestertown, Maryland, United States
$109

Put yourself in the midst of American history by staying at Mitchell House. Rest in one of the six comfortable rooms or, for added privacy, relax in the one-bedroom Stone’s Throw Cottage. This colonial house is just minutes away from Historic... more

The Imperial Hotel and Restaurant

Chestertown, Maryland, United States
$150

For over 100 years, The Imperial Hotel has stood in the historic district of Chestertown, Maryland. It offers comfortable accommodations in eleven deluxe rooms and two suites, all within walking distance of the best attractions in Chestertown. Take a walk through town for shopping, sightseeing, and Chestertown’s Washington College. Enjoy on-site... more

Knapp's Narrows Marina & Inn

Tilghman Island, Maryland, United States
$80

Knapp's Narrows Marina and Inn is located on Tilghman Island, Maryland, offering perfect access to the Chesapeake Bay.... more

Driftwood Inn

Chestertown, Maryland, United States
$60

Rest and relax at this 28-room Inn, conveniently located in peaceful Chestertown. Lounge on your spacious colonial-style bed or splash in the outdoor pool. Some rooms even feature a jacuzzi style tub! And Driftwood Inn is within easy distance of all... more

Wades Point Inn on the Bay

St. Michaels, Maryland, United States
97
Excellent
21 Reviews
$151

Wades Point Inn on the Bay Bed & Breakfast is located just outside of St. Michaels, on Maryland's Eastern Shore, and minutes from Tilghman Island, Easton, and Oxford. Our 120 acres of fields and woodland and approximately 1/2 mile of coast line overlooking the Chesapeake Bay and Eastern Bay offer a peaceful setting for relaxation and recreation.... more

Osprey Point

Rock Hall, Maryland, United States
95
Excellent
13 Reviews

Osprey Point on Maryland's Eastern Shore prrovides a luxurious northern Chesapeake Bay adventure destination located on 30 lush acres of waterfront solitude in the village of Rock Hall. The Inn provides elegant lodging and gourmet dining just a few feet away from our modern world class marina on the Chesapeake Bay's eastern shore, with the... more

Oxford Inn

Oxford, Maryland, United States
$76

The circa 1900 Oxford Inn, facing east to greet each day's dawn, is located at the head of Town Creek in Oxford's Historic District. Your stroll from the Inn to the Oxford - Bellevue Ferry Landing takes you down one of the oldest streets in America. The Oxford Inn welcomes children. The charming town of Oxford is a great destination for the entire... more

Five Gables Inn & Spa

St. Michaels, Maryland, United States
78
Good
38 Reviews
$151

Saint Michaels offers a quiet charm and a safe, peaceful haven for a day, weekend or vacation. Stroll the historic streets with homes lovingly restored, welcoming you to take a step back in time. Historic sites, enchanting Inns, Bed & Breakfasts and museums give you the feeling of what was once a thriving Colonial Village, and is now home to... more

Crystal Sands Motel

West Ocean City, Maryland, United States
85
Very Good
264 Reviews
$79

We welcome you to Ocean City. Crystal Sands Motel is within walking distance to many restaurants, shopping centers and recreational facilities we are also located only 1/2 block from the Boardwalk and Ocean.... more

Simply Bed & Bread

Chestertown, Maryland, United States
$119

With only two rooms in this quiet and comfortable guest house, you’ll feel right at home at Simply Bed and Bread. Sit on one of the inviting wicker chairs on the porch and look over Chestertown, Maryland. Inside, delicious treats like fresh... more

Swan Haven B & B

Rock Hall, Maryland, United States
$76

Swan Haven offers a quiet, relaxing waterfront getaway to the village of Rock Hall on Maryland's historic Eastern Shore, in the heart of Waterman's Country. Enjoy delightful accommodations on the water, with small boating adventures of many kinds to be had starting right at our docks. It's only a short walk to Rock Hall's many fine restaurants,... more

The Old Brick Inn

St. Michaels, Maryland, United States
86
Excellent
20 Reviews
$125

Welcome to Old Brick Inn, a Maryland boutique hotel in the tradition of a bed and breakfast. Start off your day with a tantalizing homemade breakfast and then head out to explore shopping, museums, golf and area sights, like Hooper Strait Lighthouse. Lavish rooms and suites have their own private bath and many have fireplaces and Jacuzzis. Make... more

George Brooks House Bed & Breakfast

St. Michaels, Maryland, United States
$120

Featuring six beautiful guest rooms with hand-carved mahogany furniture, lovely gardens with a pool and hot tub, and three-course gourmet breakfasts, the George Brooks House Bed & Breakfast is a Maryland B&B experience you’ll want to wake up to over and over again! The ‘Fit For a King’ room, complete with a fireplace and a veranda,... more

Showing 16-30 of 69 Resorts and Lodges

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