Eastern Shore Holidays

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Where to stay in Eastern Shore

Find the best Eastern Shore areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Shore
A Ferris wheel, a roller coaster, and a building with a sign that reads 'Holy Roller.'

Downtown Ocean City

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Ocean City, Ocean City Beach and Jolly Roger at the Pier are top sights worth seeing.

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A Ferris wheel, a carousel, and a food stall at a fair.

Midtown Ocean City

2 out of top 10 points of interest in this area

Midtown Ocean City is known for its stunning beaches, and with sights like Ocean City Beach and Seacrets Distilling Company, you won't get bored spending a day wandering around this part of Ocean City.

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A beach with a clear sky and calm sea.

Ocean Pines

You'll enjoy the beaches and live music in Ocean Pines. You might want to make time for a stop at Ocean Pines Golf and Country Club or Isle of Wight Bay.

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A marina with multiple sailboats docked.

West Ocean City

The beaches and seaside views are top of the list for many visitors to West Ocean City. A stop by Tanger Outlet Center or Ocean City Harbor might round out your trip.

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A group of horses grazing on a sandy beach with sparse vegetation.

Montego Bay

If you're spending some time in Montego Bay, Northside Park and Assawoman Bay are top sights worth seeing.

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Top hotels in Eastern Shore

Castle in the Sand

Castle in the Sand

3701 Atlantic Avenue Ocean City MD
€63
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"The bathroom was clean but a little in need of upgrades. The hotel staff were amazing so helpful and nice! Great location!"

Reviewed on 6 Oct 2026

Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
€66
29 Oct - 30 Oct
includes taxes & fees
Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD
€99
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (2,824 reviews)
"A beautiful, very clean, very comfortable room! I have stayed here before, and I definitely will again! The staff are also very friendly and helpful. Absolutely no complaints or concerns."

Reviewed on 6 Oct 2026

Princess Royale Oceanfront Resort
See all 7,679 properties in Eastern Shore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Eastern Shore attractions

A boardwalk entrance with a sign reading "Boardwalk Maryland" and two lighthouse-style structures.

Ocean City Boardwalk

9.0/10 (11,302 reviews)
This historic three-mile boardwalk has delighted visitors with ocean views and carnival charm since 1902. Savour local favourites like Thrasher's French Fries while exploring vintage amusement rides at Trimper's.
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A coastal cityscape with a sandy beach, ocean waves, and high-rise buildings.

Ocean City Beach

9.2/10 (10,973 reviews)
This classic 10-mile stretch of Atlantic shoreline pairs pristine sand with a vibrant, attraction-filled boardwalk. Enjoy free beach access year-round, with seasonal festivals adding extra charm to your coastal getaway.
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A stone wall with the text "Roland E. Powell Convention Center" and a landscaped area with trees and shrubs.

Roland E. Powell Convention Center

8.0/10 (2,358 reviews)
This modern bayfront venue hosts Ocean City's premier events, from trade shows to concerts. Enjoy panoramic water views while attending diverse exhibitions in its state-of-the-art facilities.
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A wooden boardwalk by a body of water with binoculars and a bench.

Inlet Park

8.6/10 (1,457 reviews)
Gaze across the Atlantic towards Assateague Island from this peaceful coastal viewpoint. The park's wooden "Whispering Giant" sculpture honours Native American heritage while offering wildlife spotting.
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A carousel, a large statue, and a building with a neon sign.

Jolly Roger Amusement Park

8.2/10 (3,806 reviews)
This dual-location amusement park features ocean-view rides at the Pier and thrilling water attractions at 30th Street. Enjoy illuminated attractions and panoramic Atlantic views from the Giant Wheel.
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A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.

Jolly Roger at the Pier

8.4/10 (2,874 reviews)
This lively boardwalk amusement park dazzles with iconic rides like the Giant Wheel and Looping Star Roller Coaster. Evening visits offer magical views when colourful lights illuminate against the Atlantic sky.
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Salisbury University

8.4/10 (452 reviews)
Salisbury University's picturesque campus blends historic and modern architecture. Explore the Patricia R. Guerrieri Academic Commons for panoramic views and check the event calendar for cultural performances.
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Frequently asked questions

How much does an Eastern Shore holiday package cost?
Get ready to book, because a getaway to Eastern Shore starts from an affordable . When you combine your hotels, flights and car rentals into a package, you'll pick up the biggest deals.
How do I get a cheap travel package to Eastern Shore?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into an Eastern Shore holiday package and save. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to tailor your holiday your way. We offer more than 550 airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and live out those holiday dreams.
What are the top hotels in Eastern Shore?
Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel know how to make their guests feel at home in Ocean City. If your travel plans also include Berlin, check out Fenwick Inn and Hilton Garden Inn Ocean City Oceanfront. Both are top picks with travellers.
How far in advance should I book my Eastern Shore holiday?
Savvy travellers often reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to a year before your intended flight. If you're late to book, don't worry. Bargain prices sometimes occur just weeks prior to departure.
What does an Expedia Eastern Shore travel package include?
It all comes down to what kind of getaway you're contemplating. Eastern Shore travel deals can include car rentals, hotels and flights. You can mix and match to create the package that suits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking an Eastern Shore travel package?
A travel package can be tailored to your budget and is a great way to make your hard-earned dollars stretch further. How much you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with an Eastern Shore Expedia holiday package?
With a holiday package, you're the boss. Whether you're eager to fly to Eastern Shore in first class or coach, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Eastern Shore holiday package?
Yes, you can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Eastern Shore holiday package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.