Places to Stay on the Eastern Shore

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. 

By Jim Meyer

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Featured Places

The Atlantic Hotel in Berlin
The Atlantic Hotel in Berlin
Photo By: Worcester County Tourism

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.

brightly painted Victorian hotel Photo By: Whitehaven Hotel

1 Whitehaven Hotel, Historic Bed & Breakfast

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.


More about The Whitehaven Hotel


Type:
Bed & Breakfasts and Inns


Location:
2685 Whitehaven Rd
Whitehaven, MD 21856
410-873-3099


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With a spa, golf club and proximity to outdoor activities, this resort has something for everyone.

2 Pamper Yourself at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge

Home of the River Marsh Golf Club, one of the top ten 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.


More about Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina


Type:
Conference Centers


Location:
100 Heron Blvd
Cambridge, MD 21613
410-901-1234


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Frontier Town Campground

3 Cowboy Up at 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.


More about Frontier Town Campground


Type:
Campgrounds


Location:
Rt 611, Stephen Decatur Hwy
Berlin, MD 21811
410-641-0880


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Knapps Narrows Inn and Marina

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

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.


More about Knapp's Narrows Marina & Inn


Type:
Bed & Breakfasts and Inns


Location:
6176 Tilghman Island Rd
Tilghman, MD 21671
410-886-2720


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The Robert Morris Inn

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


More about Robert Morris Inn


Type:
Bed & Breakfasts and Inns


Location:
314 North Morris St
Oxford, MD 21654
410-226-5111


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Canoe at Tuckahoe State Park Photo By: VisitMaryland.org

6 Camp Out at Tuckahoe State Park

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.

More information...

The Old Brick Inn

7 Explore St. Michael’s From 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.


More about Old Brick Inn


Type:
Bed & Breakfasts and Inns


Location:
401 S Talbot St
St. Michaels, MD 21663
410-745-3323


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The Atlantic Hotel in Berlin

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

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).


More about Atlantic Hotel


Type:
Hotels & Motels


Location:
2 N Main St
Berlin, MD 21811
410-641-3589


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Osprey Point Inn, Restaurant and Marina

9 Experience Elegance at Rock Hall’s Osprey Point

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.


More about Inn at Osprey Point


Type:
Bed & Breakfasts and Inns


Location:
20786 Rock Hall Ave
Rock Hall, MD 21661
410-639-2194


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Somers Cove Marina

10 Drop Anchor in Crisfield Harbor at 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.


More about Somers Cove Marina


Type:
Outdoor Recreation


Location:
715 Broadway
Crisfield, MD 21817
410-968-0925


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Inn at Huntingfield Creek, Rock Hall

11 Inn at Huntingfield Creek, Rock Hall

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.


More about Inn at Huntingfield Creek B&B, LLC


Type:
Bed & Breakfasts and Inns


Location:
4928 Eastern Neck Rd
Rock Hall, MD 21661
410-639-7779


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Edge Hotel at Fager's Island, Ocean City

12 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.


More about The Edge Hotel at Fager's Island


Type:
Hotels & Motels


Location:
200A 56th Street in the Bay
Ocean City, MD 21842
410-524-5400


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Historic Kent Manor Inn

13 Historic Kent Manor Inn, Stevensville

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.


More about Historic Kent Manor Inn


Type:
Bed & Breakfasts and Inns


Location:
500 Kent Manor Dr
Stevensville, MD 21666
410-643-5757


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Five Gables Inn and Spa, St. Michaels

14 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.


More about Five Gables Inn & Spa


Type:
Bed & Breakfasts and Inns


Location:
209 N Talbot St
St. Michaels, MD 21663
410-745-0100


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Assateague ponies next to tent Photo By: Frank Forgoine

15 Fall Camping at Assateague

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


More about Assateague State Park


Type:
Attraction


Location:
7307 Stephen Decatur Hwy
Berlin, MD 21811
410-641-2918


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Smith Island Inn Photo By: TripAdvisor

16 Smith Island Inn, Ewell

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 letting embracing the beauty of the Chesapeake Bay.


More about Smith Island Inn


Type:
Bed & Breakfasts and Inns


Location:
20947 Caleb Jones Rd.
Ewell, MD 21824
410-425-2650


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Lighthouse Club Hotel, Ocean City Photo By: TripAdvisor

17 Lighthouse Club Hotel, Ocean City

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.


More about Lighthouse Club Hotel at Fager's Island


Type:
Hotels & Motels


Location:
200 56th Street in the Bay
Ocean City, MD 21842
410-524-5400


Learn More
Mariners Motel Photo By: Mariners Motel

18 Mariners Motel, Rock Hall

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 the Mariner. 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.


More about Mariners Motel


Type:
Hotels & Motels


Location:
5681 S Hawthorne Ave
Rock Hall, MD 21661
410-639-2291


Learn More
Inn at the Canal, Chesapeake City

19 Inn at the Canal, Chesapeake City

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!


More about Inn at the Canal


Type:
Bed & Breakfasts and Inns


Location:
104 Bohemia Ave
Chesapeake City, MD 21915
410-885-5995


Learn More
Featured Places
The Whitehaven Hotel exterior view
01
Location:
2685 Whitehaven Rd
Whitehaven, MD 21856
Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
02
Camping photo
03
Location:
Rt 611, Stephen Decatur Hwy
Berlin, MD 21811
Inn overlooking the marina
04
Location:
6176 Tilghman Island Rd
Tilghman, MD 21671
Patio at the Robert Moris Inn
05
Location:
314 North Morris St
Oxford, MD 21654
Old Brick Inn exterior
06
Location:
401 S Talbot St
St. Michaels, MD 21663
Atlantic Hotel
07
Location:
2 N Main St
Berlin, MD 21811
Inn at Osprey Point
08
Location:
20786 Rock Hall Ave
Rock Hall, MD 21661
Somers Cove Marina
09
Location:
715 Broadway
Crisfield, MD 21817
Outside view of Inn with Sunflowers
10
Location:
4928 Eastern Neck Rd
Rock Hall, MD 21661
The Edge Hotel at Fager's Island aerial view
11
Location:
200A 56th Street in the Bay
Ocean City, MD 21842
Historic Kent Manor Inn
12
Location:
500 Kent Manor Dr
Stevensville, MD 21666
Five Gables Inn and Spa exterior view
13
Location:
209 N Talbot St
St. Michaels, MD 21663
Ponies on the beach at Assateague State Park
14
Location:
7307 Stephen Decatur Hwy
Berlin, MD 21811
Smith Island Inn
15
Location:
20947 Caleb Jones Rd.
Ewell, MD 21824
Lighthouse Club Hotel at Fager's Island
16
Location:
200 56th Street in the Bay
Ocean City, MD 21842
Mariners Motel exterior view
17
Location:
5681 S Hawthorne Ave
Rock Hall, MD 21661
Inn at the Canal exterior view
18
Location:
104 Bohemia Ave
Chesapeake City, MD 21915
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