Historic Inn

Places to Stay on the Eastern Shore

By Jim Meyer

With its welcoming small towns, bucolic farmlands and sprawling wilderness preserves, the Eastern Shore is a world apart, nestled between the Chesapeake and the Atlantic. 

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Historic Inn

Whether you’re planning a romantic retreat, a shopping safari, a camping trip with the kids or even an old west adventure, Maryland’s Eastern Shore can put you up for your perfect getaway.

1
Whitehaven Hotel, Historic Bed & Breakfast
brightly painted Victorian hotel
Whitehaven Hotel

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.

2
Pamper Yourself at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge
With a spa, golf club and proximity to outdoor activities, this resort has something for everyone.

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.

3
Cowboy Up at Frontier Town Campground
Frontier Town Campground

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.

4
Take a Break from the Bay at Knapps Narrows Inn & Marina in Tilghman
Knapps Narrows Inn and Marina

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.

5
Dine and Delight at Oxford’s Robert Morris, America’s Oldest Inn
The Robert Morris Inn

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.

6
Camp Out at Tuckahoe State Park
Paddle the Tuckahoe Creek
Christina Lippincott, Caroline Tourism

Kayakers explore the upper reaches of Tuckahoe Creek, a tributary of the Choptank River.

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.

7
Explore St. Michael’s From the Old Brick Inn
The Old Brick Inn

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.

8
Get Away to the Atlantic Hotel in Berlin, the “Coolest Small Town in America”
The Atlantic Hotel in Berlin

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).

9
Experience Elegance at Rock Hall’s Osprey Point
Osprey Point Inn, Restaurant and Marina

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.

10
Drop Anchor in Crisfield Harbor at Somers Cove Marina
Somers Cove Marina

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.

11
Inn at Huntingfield Creek, Rock Hall
Historic Inn

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.

12
Edge Hotel at Fager’s Island, Ocean City
Edge Hotel at Fager's Island, Ocean City

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.

13
Historic Kent Manor Inn, Stevensville
Historic Kent Manor Inn

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.

14
Five Gables Inn and Spa, St. Michaels
Five Gables Inn and Spa, St. Michaels

This inn is located in four historic houses. Take a short walk to nearby shops and restaurants, or spend the day exploring the Chesapeake Bay on a charter boat. Go for a swim in the indoor pool, then stop by the sauna and steam room. Your four-legged friends can join you in one of the pet-friendly rooms. Visit off-season and take advantage of their special off-season packages.

15
Fall Camping at Assateague
Assateague ponies next to tent
Frank Forgoine

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

16
Smith Island Inn, Ewell
Smith Island Inn
TripAdvisor

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.

17
Lighthouse Club Hotel, Ocean City
Lighthouse Club Hotel, Ocean City
TripAdvisor

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 relax 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.

18
Mariners Motel, Rock Hall
Mariners Motel
Mariners Motel

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 Marina. And after a long day on the water, the beautifully landscaped gazebo, complete with grills, is the perfect place to unwind.

19
Inn at the Canal, Chesapeake City
Inn porch overlooking canal
Inn at the Canal

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!