The Inns of the Chesapeake Bay: B & Bs by Boat

The only thing better than visiting the picturesque Chesapeake Bay region is enjoying it along the water by boat. Some incredible bed and breakfasts in this region cater to boaters, featuring adjacent docks and waterfront views. Whether staying for a weekend getaway at one inn or making an extended journey in the footsteps, or rather, the wake of Captain John Smith, this region offers some outstanding inns for making unforgettable maritime memories. We begin the trip from the south end of the Eastern Shore of Virginia and head northward along the Bay, with a final docking in the historic Fells Point Village within Baltimore.

Rock Hall: The Moonlight Bay Inn offers an ideal setting, right at the edge of the Chesapeake Bay and just outside of Chestertown, an upscale historic town on the Chester River.  The circa 1850 house includes a veranda lined with wicker furnishings and a swing, and the grounds boast a gazebo and English garden. Five rooms are located in the main inn; several offer outstanding bay views. The West Wing includes five bay-front rooms, all with a whirlpool bath.  Guests can  fish, golf at the nearby club, take a nature walk at one of two local wildlife preserves or root through the local antique shops. The inn features 50 boat slips on 2 well-lit docks; individual 30 amp service; water connections. There’s no charge for docking boats for guests staying two or more nights.

Cape Charles (southernmost tip of the Eastern Shore):The Cape Charles House is a Colonial Revival home built in 1912 on the site of the town’s first schoolhouse. The inn was the recipient of the Governor’s Award for Virginia B and B Hospitality and was featured on HGTV “If Walls Could Talk.”  The present owners have skillfully combined antiques, heirlooms, oriental rugs, artwork, fabrics and various collections to create a singularly eclectic, artistic style.  Visit the historic Victorian village or swim the quiet bay beach. Bikes, beach towels, chairs and umbrellas are available from the inn. Bay Creek Marina offers overnight slips and rents bikes and golf carts. However the innkeepers will pick you up at the marina if you prefer.

Smith Island:   The Inn of Silent Music.  Come down in time to peaceful, natural serenity in the quiet road-and car-free town of Tylerton– population 60. The Washington Post describes it as “Breathtaking, almost overwhelming Chesapeake Bay views, on the less populous end of barely populated Smith Island.” This is the community Tom Horton celebrated in his book, An Island Out of Time. Explore this waterman’s island village where a Colonial English/Cornish dialect is still spoken. Or leave your boat behind and ferry into Crisfield to explore the historic towns of Princess Anne and Snow Hill. 
Private dock at the inn for shallow draft boats; town dock for deep-draft boats (the inn will pick you up).

Oxford:   Immerse yourself in colonial history at the Robert Morris Inn, one of the oldest historic inns in the United States, dating back to 1710.  Just off the Bay on the Tred Avon River, the majestic colonial inn sits across from the town dock and ferry in the quaint village of Oxford, Maryland, known for its generations of boat builders.  Legend has it that Michener wrote the outline for his book Chesapeake while staying at the inn. The Robert Morris Inn is only 7 miles from St. Michaels, 10 miles from Easton and Cambridge.

Tilghman Island: Located on 57 beautiful acres set aside as a wildlife sanctuary facing the river opening to the Chesapeake Bay,
Black Walnut Point Inn is a handsome circa 1843 Colonial Revival manor house commanding waterfront views from its private peninsula location with private dock. From its bayside hammock to its nature walk and swimming pool, the inn provides an amazingly private getaway. Accommodations are in the main house as well as the Riverside Cottages which have their own living room, fireplace, private bath, and kitchen and water view porch.

Stevensville:  Spanning 226 woodland acres with more than one mile of waterfront on a tributary to the Chesapeake Bay, the circa 1820 Kent Manor Inn  includes a gourmet restaurant, 24 luxurious rooms, outdoor Olympic-size pool, pier, paddleboats and  bikes for guest use. Stroll on a walking path, play a lawn game or relax on the veranda. Some of the elegant rooms at the inn contain four-poster beds, Italian marble fireplaces, balconies and walk-out porches. 

Annapolis: One of the oldest towns in the United States, one can spend hours if not days taking in the historic architecture, the waterfront, the historic State House Rotunda, the Naval Academy and it’s impressive maritime museum and the myriad shops, galleries and fine restaurants. There are countless B&Bs in the area within blocks of the town dock. Check with each innkeeper to see if they have pickup service to bring you and your luggage to the inn. Around the Annapolis City Dock area you will find the Market House, harbormaster’s office, work boats, tour boats, pleasure craft and visiting ships.   In the summer, enjoy Navy band concerts and festivities. In the fall, the largest boat shows in the world are held at the Annapolis City Dock. During the holidays, enjoy a glittering display of sailboats adorned in lights.

Baltimore:   Celie’s Waterfront Inn is in a charming circa 1880 waterfront home. It is located in the historic harborside village of Fells Point, with its cobblestone streets and quaint shops.  As you stand out front of Celie’s, you will be looking directly at the building where the famous hit series “Homicide: Life on the Streets” was filmed,  next to other landmarks such as The Wharf Rat, The Horse You Rode In On, Jimmy’s and The Daily Grind, also featured on the award-winning television series. Guest bedrooms feature a whirlpool, fireplace, skylight, private balcony or courtyard. There are also family suites which boast kitchens and access to the roof deck.  Boaters can anchor off the Broadway Pier directly across the street from the inn. 

Still undecided? Browse through the 19,000 B&Bs and country inns that specialize in other events that may interest you. Many of the properties listed above are also in the best-selling bed and breakfast guidebook Bed & Breakfasts and Country Inns with a Buy-One-Night-Get-One-Night-Free Certificate. ILoveInns also offers Bed and Breakfast Gift Certificates, a perfect solution to help celebrate any occasion.