Places to Stay on the Eastern Shore

Situated in a charming village by the Whitehaven Ferry, the Hotel is only minutes from the Chesapeake Bay. The Whitehaven Hotel, one of the last of its kind, once provided lodging for travelers crossing the Wicomico River by horse and by steamship to ports as far as Baltimore.

Home of the River Marsh Golf Club, one of the top 10 courses in the North East according to Conde Nast, this beautiful resort along the banks of the Choptank River has it all. Use the resort as a home base for exploring the nearby Blackwater National Wildlife Refuge. Or, you don’t even have to leave the Hyatt’s 400 luxurious waterfront acres—with tennis pros, world class dining, watersports and all-inclusive packages available, it’s paradise on the shore.

Visiting by boat? Grab a slip at Knapps Narrows’ 1,000-foot floating dock in Tilghman, or come by car and get a room at the inn. Go for a lighthouse tour, a fishing charter, or take a sunset cruise on a historic ketch and watch the skipjacks bring the bay’s harvest home.

Built in 1710 when Maryland was still a British colony, the Robert Morris Inn is older than the nation around it! The waterfront grounds are perfect for enjoying a summer’s breeze, and the charming rooms with their roaring fires make ideal respites from winter’s chill. Take the ferry for a day in St. Michaels, then dine at the inn and experience the culinary wonders of celebrity chef Mark Salter.

Camp and canoe under the forested canopy of the upper Tuckahoe River, venture into the Choptank, or paddle with the family in Tuckahoe Park’s 60-acre lake and enjoy a wilderness getaway. Tuckahoe State Park offers fantastic wildlife viewing and the convenient campground even has a tire park for the kids.

If you want to explore the shops, restaurants and easy living of St. Michaels, put yourself into the heart of it all at the Old Brick Inn. The Old Brick Inn offers luxurious rooms and modern amenities in an historic setting. Plus, since it’s located downtown, the boutiques are just a stroll away.

This Victorian retreat is an absolute gem in the middle of downtown Berlin. Wander the charming, walkable streets and let the locals show you why Berlin was named “Coolest Small Town in America” by Budget Travel. Make sure to hit the hotel restaurant with its modern takes on classic shore cooking (the rockfish is not to be missed).

Luxuriate on the shores of Swann Creek at this beautiful inn and full service marina. Just a stone’s throw from Rock Hall and its legendary seafood, the manicured grounds of Osprey Point are an idyllic getaway spot just a short drive from Baltimore, Washington, D.C. and Philadelphia.

Looking for the perfect place to stay for the legendary Hard Crab Derby, or just want to live the islander life for a spell? Somers Cove Marina is the perfect port. This full service marina is right in the heart of downtown Crisfield, so it’s easy to see the town as well as explore Tangier Sound with its amazing saltwater fishing.

Pitch your tent or park your motorhome at this Woodall’s 5W-rated campground on the shore of the Sinepuxent Bay. With a high ropes course, miniature golf, a waterpark and the legendary Old West show, Frontier Town has been a Maryland Tradition since 1959. And best of all, it’s city-close and country-quiet, smack dab in the middle between Assateague and Ocean City.

From October through mid-March, campsites are available first-come, first-served, making Assateague National Seashore a perfect spontaneous getaway for early-birds. Let the sounds of surf and sea carry you to sleep. Let the unforgettable vistas dotted with the island’s famed wild horses inspire you to a day’s adventure. And check nearby NASA Wallops Island’s rocket launch schedule for a truly out of this world experience.

Rejuvenate in quiet luxury and enjoy breathtaking Chesapeake Bay views at this well-appointed boutique Chestertown hotel. Housed in a 12,000-square-foot Georgian-style manor with 12 uniquely decorated rooms and a Carriage House suite, Great Oak Manor has all you need for a relaxing getaway by the Bay. All the rooms have king-sized beds and private bathrooms and a few have fireplaces.The onsite restaurant offers a locally-focused, farm-to-table menu, with dining inside or al fresco overlooking the Grand Lawn. Nearby historic Chestertown with galleries, shops and restaurants exudes elegant small town charm.

This stunning waterfront property, first built in 1820 and refurbished, sits on 220 acres of farmland, woods and waterfront, with 24 guest rooms. Wander the grounds for picturesque water views and gardens. The inn provides a fresh complimentary deluxe continental breakfast for guests, and there’s a Sunday champagne brunch buffet, too.

These sophisticated rooms in 12 distinctive suites have one thing in common: the awe-inspiring views of the Bay through their expansive windows. There’s also easy access to Fager’s Island Restaurant, which has an extensive craft beer menu and second-to-none sunset views.

Outside magazine called the Smith Island Inn one of its “28 Best Trips of 2016,” and it’s little wonder why. With stunning views from this harbor front vista, a stay at the Smith Island Inn means becoming an islander for a few days and embracing the beauty of the Chesapeake Bay.

Book one of the stunning, bayfront suites at this Fager’s Island getaway for a unique perspective on OC. Escape for one of their winter romance and relaxing island escapes, or the famous New Year’s Eve Party Package. Or just make it that serene escape on your beach week adventure. You can’t go wrong at The Lighthouse.  

Water and nature lovers will find paradise here. Take a relaxing walk on the nearby trails through meadows and forests, then return to your guest room or fully-furnished private cottage. Visit the nearby Waterman’s Museum and learn about one of Maryland’s most vital and historic industries, then stop at Waterman’s Crab House and Dock Bar to taste the succulent seafood resulting from that labor.

Nestled within 35 acres of lush, landscaped gardens, meadows, and forest on Maryland’s Eastern Shore, the Brampton Inn is a stone’s throw from the quaint town of Chestertown and the scenic Chester River. The historic inn offers 13 unique accommodations, including seven spacious rooms and suites in the stately 1860 manor house and six cozy private cottages. Breakfast at the Brampton Inn features fresh, locally sourced ingredients and changes daily.

If you’ve never made the trip to Chesapeake City, a historic, walkable town on the banks of the Elk River, you need to change that soon. And there’s no better place to stay than the Inn at the Canal. This seven-room Victorian B&B is just steps away from the Ben Cardin C&D Canal Trail, and an easy stroll to Chateau Bu-De, where classic French cooking meets unforgettable Chesapeake flavors. Plan your trip now!

Set in idyllic Tangier Sound and home to more than 2,900 acres of saltmarsh, more than 30 miles of water trails, and pristine, isolated beaches,  Janes Island State Park is a unique island getaway on the Chesapeake Bay just outside of the historic town of Crisfield. Even better, there are 103 campsites, perfect for pitching a tent as eagles turn in the sky above!

Tucked away on a secluded point on Tilghman Island, the Black Walnut Point Inn  is one of the most unique spots on the Chesapeake Bay. A gate secures the half-mile drive through 52 acres of bird sanctuary before opening to six acres of wildflower gardens and lawn surrounded by water. Enjoy the quiet side of the Bay with eagles, osprey, butterflies, waterfowl, dolphin, otters and rays as your only “neighbors.” Catch the sunrise over the Choptank River and take in the sunset over the Chesapeake Bay without ever leaving your island getaway. You can choose a room in the 1840s House or settle in for a relaxing stay at one of three themed cabins (complete with fireplaces and full kitchens). The Inn serves only breakfast, so head to Two if By Sea,  Tickler's Crab Shack or the Tilghman Island Inn for nearby lunch and dinner options. Venture a few miles further to the charming town of St. Michaels for more dining and entertainment options.

Simple, old-school, and awesome. If you’re looking to get away to Rock Hall, the Mariners Motel is perfect for families looking for a great place at a reasonable rate. Fishermen and outdoors enthusiasts will love Mariners. It’s the perfect spot for Rockfish season, located right next door to the Rock Hall Landing Marina. And after a long day on the water, the beautifully landscaped gazebo, complete with grills, is the perfect place to unwind.