Bed and Breakfasts in the Northern Chesapeake Bay Region(Including Havre de Grace, North East, Chesapeake City, Betterton, Rock Hall, and Chestertown) Chesapeake City: Inn at the Canal. Waterfront views. Six private rooms with private baths. 104 Bohemia Ave, Chesapeake City, MD. B&B Website Blue Max Inn Bed and Breakfast. An 1854 inn located in the heart of the town's historic area. 300 Bohemia Ave, Chesapeake City, MD. B&B Website Ship Watch Inn. Renovated home located along the Chesapeake and Delaware Canal waterfront. All rooms face the water. 401 1st Street, Chesapeake City, MD. B&B Website 
Chestertown: Brampton Bed & Breakfast Inn. Located on 20 wooded acres, just one mile outside of Chestertown, Maryland. 25227 Chestertown Road, Chestertown, MD 21620. B&B Website Great Oak Manor Inn. Waterfront bed and breakfast on the outskirts of Chestertown. B&B Website The Inn at Mitchell House. Located between Chestertown and Rock Hall in Kent County. An 18th Century manor house on 12 manicured acres. B&B Website Lauretum Bed & Breakfast Inn. This 1881 home sits on six acre property in Chestertown. B&B Website. Simply Bed and Bread. Located 100 yards from the Washington College campus and a 10 minute walk to downtown Chestertown. B&B Website Widow's Walk Inn. In Chestertown's historic district. Within walking distance of the Chester River, Washington College, shops and restaurants. B&B Website White Swan Tavern. A restored historic inn. B&B Website North East: North Bay Bed & Breakfast. Nautical setting, Harbor view, and waterside accommodations. Everything sailing with a bit of power boating. Delicious full breakfast. North Bay, experience the Bay lifestyle. 9 Sun Set Drive, North East, MD 21901. B&B Website Havre de Grace: La Cle D'Or Guest House. Historic Hopkins House in Havre de Grace. Three suites with private baths. B&B Website Spencer-Silver Mansion. An 1896 Victorian mansion decorated in period style. Located in the historic district, a few blocks from the Concord Point lighthouse and the decoy museum. B&B Website Vandiver Inn. An 1886 Victorian mansion located just blocks from the Chesapeake Bay. Two adjacent guest houses provide additional rooms. B&B Website Rock Hall:The Black Duck Inn and Dockside Cafe. 21906 Chesapeake Ave. Rock Hall, Md. Overlooks Rock Hall harbor. Complimentary dockage for guests arriving by boat. B&B Website The High Tide Inn. 20828 Rock Hall Ave. Rock Hall, Md. Next door to Haven Harbour Marina and within walking distance of downtown. B&B Website Inn at Huntingfield Creek. 4928 Eastern Neck Road. Rock Hall, Md. Located on an historic waterfront farm estate. B&B Website Osprey Point Inn, Restaurant and Marina. 20786 Rock Hall Ave. Rock Hall, Md. 30 acre waterfront property with Inn, marina, and gourmet restaurant. B&B Website Inn at Swan Haven. 20950 Rock Hall Ave. Waterfront Inn. Walking distance to downtown. B&B Website Tallulah's on Main. 5720 Main Street. Rock Hall, Md. Located on Main Street, close to restaurants and shops. B&B Website Bed and Breakfasts in the Central Maryland Chesapeake Bay Region(Including Baltimore, Annapolis, and Edgewater) Baltimore: Abacrombie Inn. Historic Bed & Breakfast with award winning restaurant. Located in the heart of the cultural center, close to public transportation. The Meyerhoff Symphony Hall is across the street and Lyric Opera House is two blocks away. 58 West Biddle St., Baltimore, MD 21201. B&B Website Annapolis:Academy Bed and Breakfast In the heart of downtown Annapolis, steps to city dock and restaurants. B&B WebsiteThe Annapolis Inn An historic landmark townhouse on Price George Street in the heart of the Annapolis historic district. B&B WebsiteAnnapolis Royal Folly Located in the heart of Annapolis historic district. Steps from the Naval Academy, state capital, shops and restaurants. B&B WebsiteAnnapolitan Bed & Breakfast Centrally located in historic downtown Annapolis. Close to Naval Academy Stadium. B&B WebsiteCharles Inn Restored Civil War era home. In the heart of the Annapolis historic district. B&B WebsiteChez Amis Bed & Breakfast Located in the heart of the Annapolis historic district. Four bedroom bed and breakfast. B&B Website Flag House Inn Located 1/2 block from the City Dock and Naval Academy visitor's gate 1. B&B Website Gibson's Lodgings Three houses on the same property with a total of 20 guest rooms. 1/2 block from City Dock and right next to the Naval Academy. B&B Website Harbor View Inn of Annapolis On St. Mary's Street in heart of this historic district. B&B Website Inn at Horn Point 100 Chesapeake Avenue. Annapolis, MD. Located in the village of Eastport, within walking distance of shops and restaurants. Water taxi available three blocks from the inn. B&B Website Peninsula House Bed & Breakfast. Just steps away from the Chesapeake Bay, Historic Annapolis Harbor, the US Naval Academy and numerous museums and wonderful shops. 11 Chester Ave., Annapolis, MD 21403. B&B Website Schooner Woodwind Boat & Breakfast. Sleep aboard a classic wooden 74-foot schooner. Package includes two-hour sunset sail, overnight accommodations in a private, air conditioned, stateroom with double double berth, and deluxe continental breakfast. Great downtown location! 80 Compromise Street, Annapolis, MD 21401. B&B Website Bed and Breakfasts in the Southern Maryland Chesapeake Bay Region(Including Solomons Island, St. Mary's, and Chesapeake Beach) Solomons:Back Creek Inn. Overlooks the water. Six rooms and a private cottage. B&B Website Blue Heron Inn. Solomons Island Road bed and breakfasts. Water views. B&B Website Solomons Victorian Inn. Charles and Maltby Streets. Marina views. B&B Website Bed and Breakfasts in the Virginia Northern Neck & Middle Peninsula Region(Including Reedville, Urbanna, Gloucester, Colonial Beach, Irvington, and Mathews) Gloucester: The North River Inn, a Waterfront Bed & Breakfast. Surrounded on three sides by salt water, the North River Inn spreads luxuriously across one hundred acres of Virginia countryside in the historic Tidewater region off the Chesapeake Bay, VA. P.O. Box 695, Route 622 (Toddsbury Lane). Gloucester, VA 3061. B&B Website
Irvington: Hope and Glory Inn. A top-rated inn located in an historic schoolhouse. Six schoolhouse rooms and six garden cottages. B&B Website Reedville: Fleeton Fields Bed & Breakfast. Located in nearby Fleeton in a waterfront, park-like setting. B&B Website The Gables. Five-story mansion located in Reedville's historic district. B&B Website Ma Margaret's House Bed & Breakfast. A lovingly restored grandmother's home. B&B Website Urbanna: Atherston Hall Bed and Breakfast. A restored schooner captain's home, located just steps from the waterfront. B&B Website The Chesapeake Inn. A boutique hotel with thirteen suites, located in the heart of Urbanna. B&B Website Upper Eastern Shore Chesapeake Bay Bed and Breakfasts(Includes Kent Island, Stevensville, Easton, Cambridge, St. Michaels, Tilghman Island, and Oxford) Cambridge:Cambridge House Bed & Breakfast. Located in the historic district, this sea captain's manor has six large guest rooms with private baths. Walk to the marina, specialty shops, restaurants, art galleries, museums and antiques. 112 High Street, Cambridge, MD 21613. B&B Website Killarney B Inn B. On the shores of the Choptank, within easy walking distance of the public fishing pier and Sailwinds Park. 102 Killarney Road, Cambridge, MD. B&B Website Lodgecliffe on the Choptank Bed & Breakfast. A gracious turn-of-the-century country home perched on a bluff overlooking the Choptank River. 103 Choptank Terrace, Cambridge, MD. B&B Website Mill Street Inn Bed & Breakfast. Restored Victorian home in the heart of the historic district is just a half block to the river and a short walk to restaurants, shops, and galleries. 114 Mill Street, Cambridge, MD. B&B Website Easton:Bartlett Pear Inn. Restored inn with restaurant and cocktail lounge. B&B Website Bishop's House Bed and Breakfast. Restored home located on a large lot in Easton's historic district. B&B Website Chaffinch House Bed and Breakfast. Queen Anne Victorian located in the historic district. Within easy walking distance of shops. Easton's Promise. Five room bed and breakfast. On Goldsborough Street. B&B Website Inn at 202 Dover. Historic mansion built in 1874. Located a short block from downtown shopping, galleries, and theater. B&B Website John S. McDaniel House. Victorian home. Short walk to downtown. B&B Website Miles River Guest House. Located outside of Easton on the banks of the Miles River. B&B Website Oxford:Combsberry Inn Bed and Breakfast An historic 1730 English Country Manor home on 30 acres of waterfront property. B&B Website Robert Morris Inn. A historic colonial country inn located on the Tred Avon River. Within walking distance of the Oxford-Bellevue Ferry. B&B Website Ruffled Duck Inn. Located in Oxford's historic district. B&B Website Sandaway Waterfront Lodging. An 1875 Victorian mansion on the water with a sandy beach. B&B Website St Michaels:Aida's Victoriana Inn. An 1865 home on the historic harbor of St. Michaels. Within walking distance of most attractions. Bay Cottage Bed & Breakfast. 26640 Yacht Club Road, St. Michaels. Waterfront B&B on a quiet point of land. B&B Website The Cherry Street Inn. 103 Cherry Street, St. Michaels. Downtown B&B. B&B Website Dr. Dodson House Bed & Breakfast. Brick home in the historic district, near the harbor. B&B Website Five Gables Inn & Spa. 209 N. Talbot Street, St. Michaels. Historic inn with spa tubs, indoor pool, sauna, and steam room. B&B Website Folly's Cove Bed & Breakfast. Waterfront B&B with swimming pool fronting on Domingo Creek, just outside of St. Michaels. B&B Website George Brooks House B&B. Restored historic home just outside of town on eight acres with swimming pool. St. Michaels. B&B Website
Hambleton Inn. 202 Cherry Street, St. Michaels. Downtown B&B. B&B Website The Old Brick Inn. 401 S. Talbot Street, St. Michaels. Circa 1816 inn located in the heart of St. Michaels. B&B Website Parsonage Inn. 210 North Talbot Street, St. Michaels. Downtown B&B. B&B Website Point Breeze Bed & Breakfast. 704 Riverview Terrace, St. Michaels. Waterfront B&B. B&B Website The Snuggery Bed & Breakfast. 203 Cherry Street, St. Michaels. Downtown B&B. B&B Website Tarr House B&B. 109 Green Street, St. Michaels. Restored home in downtown St. Michaels, overlooking the harbor. B&B Website Two Swans Inn. 208 Carpenter Street, St. Michaels. Waterfront B&B on the St. Michaels Harbor. B&B Website Wades Point Inn on the Bay. Enjoy the serenity of the country and the splendor of the Bay at our Bed and Breakfast. All rooms have air conditioning, water views, private baths, breakfast included. 10990 Wades Point Road, St. Michaels, MD 21663. B&B Website Tilghman Island: Chesapeake Wood Duck Inn. Award-Winning Chesapeake Bay Lodging on Tilghman Island. This romantic getaway brims with historic charm and gracious hospitality. The Inn offers a pristine waterfront setting, immaculate accommodations and gourmet Cuisine. Gibsontown Rd. at Dogwood Harbor, Tilghman Island, MD 21671. B&B Website Lower Eastern Shore Chesapeake Bay Bed and Breakfasts(Includes Crisfield, White Haven, Onancock, and Cape Charles) Cape Charles:The Baywood Bed and Breakfast. Located out-of-town, one mile north of the Chesapeake Bay Bridge Tunnel. B&B Website Cape Charles House. Downtown Cape Charles B&B, located on Tazewell Ave. B&B Website Chesapeake Bay View Bed & Breakfast. Located across from the beach with sunset views. 212 Bay Ave, Cape Charles, VA. B&B Website Fig Street Inn. Boutique-style inn located in historic Cape Charles. Walking distance to shops and restaurants. 1/2 mile to the Bay and beach. B&B Website Crisfield:My Fair Lady Bed and Breakfast. A fully renovated Queen Ann Victorian-style home. Five rooms with private baths. B&B Website Marquis Manor Bed and Breakfast. Located in Crisfield's historic area. Caters to outdoor activities. B&B Website Onancock:Charlotte Hotel and Restaurant. A boutique hotel in the heart of Onancock. Fine dining restaurant and full service bar. Hotel Website Colonial Manor Inn. Located on a large lot in downtown Onancock. The oldest operating inn on the Eastern Shore. B&B Website The Inn at Onancock. Renovated Eastern Shore home with five guestroom, each with private spa-style bathrooms. Located just down the street from shops and restaurants. B&B Website The Inn and Garden Cafe. Located on Market Street, a short walk to shops and restaurants. On-site fine dining restaurant. B&B Website Spinning Wheel Bed and Breakfast. Five room bed and breakfast. Located on North Street, just down the street from restaurants and shops. B&B Website Princess Anne, MD:The Somerset House Bed & Breakfast. In the historic town of Princess Anne, Maryland. A casually elegant reminder of times gone by, with period antiques, brilliant chandeliers, soaring ceilings, and Eastern Shore hospitality. B&B Website Smith Island, MD: Chesapeake Sunrise B&B. Located next to the Smith Island Marina. Breakfast included. The Inn of Silent Music. Located in Tylerton and open April 1st through November 1st. All rooms have a water view. A gourmet breakfast is included, and a local seafood dinner is also available. Smith Island Inn. A quaint B&B on historical Smith Island offering private suites with full baths, full gourmet breakfast, canoes, bicycles, birdwatching, and beautiful sunsets. Weekend Smith Island Cake demonstrations. Families, singles, and couples welcome. Susan's on Smith Island Bed & Breakfast. A two bedroom rental with beautiful views of the Chesapeake Bay. Enjoy a home cooked breakfast on the front porch.
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