Enter your name and email to receive alerts when new vacation deals are added to any property in this region.
By clicking "Submit" you are agreeing to the
Terms of Service.
Alert successfully created!
Showing 31-45 of 67 Resorts and Lodges
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
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
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
Once home to Robert Morris, the famous "Financier of the American Revolution," a stay at the historic Robert Morris Inn is a 300-year step back in time. Marvel at its beautiful timber beams, paneled walls, and elegant decoration. And, enjoy luxurious accommodations, featuring panoramic views and four-poster beds, and dine in style at Salter's Tap... more
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
Cottage at Long Haul Creek is a newly renovated 3 BR waterfront home with old-fashioned charm. Situated on 6 acres, it is located just 1/2 mile from historic St. Michaels, MD,on the Chesapeake Bay. A maritime atmosphere is just a quick walk or bike ride away from this year round vacation home. Launch/sail your boat from the backyard pier, take a... more
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
Five beautifully furnished rooms, each with its own private bath, await you at Lauretum Inn Bed and Breakfast. Savor a delicious continental breakfast, then take one of the inn's bikes for a spin. And, as a guest to Lauretum Inn, you are entitled to... more
At Lowes Wharf Marina Inn in Sherwood, Maryland, a cross road connects you with your awaiting sunset island on the Chesapeake Bay. Our accommodations feature new waterfront guestrooms, transient slips, fishing, crabbing,kayaking, or just sitting back in the yacht club having a cool drink while watching the sunset. We are only 7 miles from St.... more
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
Harbourtowne Golf Resort & Conference Center is a relaxing getaway for the entire mid-Atlantic area. Its pristine 153-acre Chesapeake Bay location is an all-waterfront escape that's not too far from home. It's perhaps the most family-friendly destination in St. Michaels with 111 luxury rooms. Charming Colonial history blends into today's resort... more
The Tarr House, circa 1667, recalls the quiet elegance of a time past. Guests are lavished with English fabrics and antiques in the richly decorated home of a professiona interior designer. The cozy sitting room features original heart-of-pine floors, a fireplace and windows framing a view of picturesque St. Michaels Harbor. Lodging rates in-... more
The Lazyjack Inn, an 1855 waterfront home, located in the village on Tilghman Island, is within walking distance to fine restaurants and antique shops and will take you back in time. The guest rooms are spacious and comfortably elegant, appointed with Antique quilts and furnishings. Tilghman Island is the home of the last working sailing fleet in... more