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The Oaks Waterfront Inn & Events
Located on an inlet of the Chesapeake Bay, minutes from St. Michaels, The Oaks offers spacious guest rooms, extraordinary waterfront event facilities, renowned cuisine and detail oriented service.
Old Brick Inn
An elegant 20-room boutique hotel in the heart of St. Michaels. We feature wine tastings, a beautiful courtyard to relax in and a delicious gourmet breakfast to start your day!
Captain's Watch Vacation Cottage
Waterfront cozy 2 bedroom cottage, screened porch, full kitchen, hot tub, kayak launch, all amenities in the quaint fishing village of Tilghman Island. Free WiFi, gas grill, fish and crab off the doc
Tidewater Vacations - Waterfront Rental Homes
Our inventory of vacation homes is on a par with the luxury and comfort offered in the Hamptons. All our exclusive, prestigious waterfront homes have private pools, docks, and some have tennis courts.
St. Michaels Inn
Comfortable Rooms, Free Breakfast, Convenient Location and an Affordable Price. Shuttle Service, Outdoor pool, & pet-friendly
Wylder Hotels - Tilghman Island
The Wylder Hotel Tilghman Island, located on a 3-mile island on the Chesapeake Bay, is a remake of an iconic property. It is an all-season escape that honors hardworking fisherman of yesteryear.
Lowes Wharf Marina Inn
Join Lowes Wharf Marina and Inn and enjoy spectacular sunsets on the Chesapeake Bay! Waterfront accommodations, restaurant, marina, kayaks and beach.
St. Michaels Harbour Inn & Marina
St. Michaels Harbour Inn, Marina & Spa is a full-service resort situated right off the Miles River in the Eastern Shore resort town of St. Michaels, Maryland.
Aida's Victoriana Inn
Adjacent to Honeymoon Bridge and the Chesapeake Bay Maritime Museum in the heart of Historic St. Michaels. Walking distance to all the attractions. Come sit back and enjoy life for a while.
Five Gables Inn & Spa
Five Gables Inn and Spa: ''Quintessential Chesapeake Bay Getaway'' consisting of three charming 19th century homes, capturing the essence of a luxurious, yet comfortable getaway with an Aveda Spa.
Snuggery Bed & Breakfast
Beautiful and cozy restored historic home (ca.1665), steps to harbor, shops and restaurants. Suite with wood burning fireplace, CAC, private baths. Join us on our front porch - a great place to relax!
Wades Point Inn
An historic country waterfront Bed and Breakfast Inn, with sweeping views of both the Chesapeake Bay and the Eastern Bay ~ beautiful Sunrises and Sunsets ~ only 5 minutes from St Michaels.
Tarr House Bed & Breakfast
Enjoy the charm and hospitality of one of the oldest restored homes in the heart of St. Michaels. Located across from the park with Harbor views and walking distance to shops, restaurants and museums.
Tilghman Island Marina & Rentals
Rent WaveRunners/Jet-Skis, Power Boats, Sailboats, Kayaks, Stand-up Paddleboards, Bikes, Fish/Crabbing Gear. Kayak our scenic nature trails. Free training/certification. Just minutes from St. Michaels
Knapps Narrows Marina & Inn
Full service marina with easy docking on our 1000' floating dock and 20 room inn overlooking picturesque waterway out to the Chesapeake Bay. Restaurant. Pool. Wifi. Meeting Rooms. Fuel Dock.
Inn at Perry Cabin
Tucked along a private corner of the Chesapeake Bay, Inn at Perry Cabin and its award-winning restaurant Stars remain the only Forbes-rated destinations on the Eastern Shore.
Point Breeze B&B
Point Breeze B&B, a waterfront bed and breakfast in St. Michaels, MD, offers a residential Bed & Breakfast experience not to missed. Full breakfast, complimentary bicycles & kayaks. Relaxing elegance.
Grandview Cottages
Charming cottages and 4 bedroom main house on Broad Creek about 5 miles from town. In-ground pool and waterfront access for crabbing with 14' rowboats for guest use. Available all year.
Chesapeake Bay Real Estate -Plus LLC-
Chesapeake Bay Real Estate Plus - Dawn Lednum Owner/Broker. The Biggest, Little Office in St. Michaels! We ARE your local realtors. Let us show you what's for sale! You're Going to Love It Here!
Eastern Shore Vacation Rentals
Largest selection of vacation homes in St. Michaels and surrounding areas. Weekly and Weekend vacations, year round. Waterfront homes, private pools and docks, cottages and pet friendly homes.
Black Walnut Point Inn
A secret place of peace, Black Walnut Point Inn is a unique six acres of gardens and lawn surrounded by the Chesapeake Bay. The sanctuary's wind and waves restores what is robbed by everyday life.