Great getaways begin here, where the pineapple truly signifies welcome, and where visitors will experience Eastern Shore hospitality at its finest.

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.

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.

Enjoy and cozy into this 1947 Cape Cod home. Nestled in a quiet neighborhood of Chestertown, the Inn is ideally located. You can easily stroll downtown or visit historical sites in the area.

Tucked away on the outskirts of Chestertown, MD, our magnificent 18th century county style estate rests alongside the waterfront of the Chesapeake Bay. With 12 guest rooms,Great Oak Manor offers the finest in a romantic luxury Inn.

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.

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!

A souly unique experience in bed and breakfast accommodations – Calm, Peace, Sleep, Conversation, Inspiration, Laughter and The Resolve to Better Look After – YOURSELF! A place where "passions" rule, encouraging of our each unique and gifted tools.

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!

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.

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.

Come relax at our elegant 1860s riverfront country home in historic Snow Hill. Canoe or bike inn-to-inn. Enjoy Maryland's eastern shore, beaches, bayou, AARP. 8 rooms and suites.

Harris Cove Cottages has eight cottages. Six cottages are individual and form an echelon of sailors saluting our picturesque private driveway. The other two sit majestically as a centerpiece on two acres of bulkheaded waterfront property.

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.

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.

Welcome to the Parsonage Inn Bed and Breakfast, a unique brick Victorian in this National Historic District. Within walking distance of the maritime museum, shops and restaurants. Top rated and recommended.

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. Perfect location for weddings and special events.

Restored Gothic Revival Victorian home built in 1908 was designated an Historic Site by Talbot County in 2001. This important county landmark was among two homes selected in 2003 by the State of Maryland for its prestigious "Preservation Award".