Eastern Shore Vacation Packages
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Your Eastern Shore Vacation
Plan a vacation package to Eastern Shore and travel on your own terms. You'll fall in love with its nature, family-friendly attractions and history. With so many things to see and do on a trip to Eastern Shore, it can be difficult to know where to begin. Kick off your journey in Ocean City at Ocean City Boardwalk and Ocean City Beach — two popular attractions here. Another top city worth adding to your itinerary is Salisbury. Don't miss Wicomico Youth and Civic Centre and Salisbury Zoo. Whether you're planning to travel for a week or a month, Expedia are here to help you customize your next Eastern Shore vacation.
Top Eastern Shore Vacation Deals
Price found within the past 48 hours. Click for updated prices.
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
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.
Ocean Pines
Boasting the largest concentration of retirees on the Eastern Shore, this community offers the Ocean Pines Golf Club, designed by Robert Trent Jones, and 13 parks, including White Horse Park. Enjoy golfing, park visits, and a peaceful atmosphere.
Midtown Ocean City
2 out of top 10 points of interest in this area
Midtown Ocean City is beloved for its stunning beaches. Take some time to explore sights in the area like Ocean City Beach and Seacrets Distilling Company.
West Ocean City
Discover fishing charters, boating, and marinas in this census-designated area, located across the Sinepuxent Bay from Ocean City. Shop at Outlets Ocean City and easily access the beach resort town via the Harry W. Kelley Memorial Bridge.
Sunset Island
While there might not be top attractions in Sunset Island, you can explore the larger area and discover places like Seacrets Distilling Company and Seacrets.
Ready to book your vacation to Eastern Shore?
Eastern Shore Hotel Deals
Princess Royale Oceanfront Resort
Oceanfront on 91st Street Ocean City MD
CA $188
CA $233 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,625 reviews)
"Pool area needs improvement! Lots of sand in the water which made the water very chalky"
Reviewed on Aug 8, 2026
Fenwick Inn
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
CA $124
CA $160 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,074 reviews)
"Dirty. Hair in sheets, hair in tub, hole in ceiling."
Reviewed on Aug 8, 2026
Grand Hotel Ocean City Oceanfront
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
CA $214
CA $240 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (3,751 reviews)
"Clean room, great staff, good breakfast"
Reviewed on Aug 8, 2026
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
Ocean City Boardwalk
9.0/10 (11,302 reviews)
Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.
Ocean City Beach
9.2/10 (10,973 reviews)
Swim in the waves of the Atlantic Ocean, relax on soft white sands or stroll by the arcades and shops on the exciting boardwalk at this family-friendly city beach.
Jolly Roger Amusement Park
8.2/10 (3,806 reviews)
Bring your family to Jolly Roger Amusement Park and have a fun-filled day at this theme park in Ocean City. Amble around this family-friendly area's seaside, or seek out the golf courses.
Roland E. Powell Convention Center
8.0/10 (2,358 reviews)
Learn about the events happening at Roland E. Powell Convention Center during your trip to Ocean City. Stroll along the seaside or discover the beautiful sunsets in this family-friendly area.
Inlet Park
8.6/10 (1,457 reviews)
Explore the lovely green spaces of Inlet Park and enjoy the golf courses in Ocean City. Stroll along the beautiful beaches or discover the area's beautiful sunrises.
Frontier Town Water Park and Golf
9.0/10 (2 reviews)
Bring the kiddos to Frontier Town Water Park and Golf and have a fun-filled day at this theme park in Berlin. Stroll along the seaside in this family-friendly area, or seek out the golf courses.
Frequently asked questions
How much does an Eastern Shore vacation package cost?
Get ready to book, because a getaway to Eastern Shore starts from an affordable CA $895. 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 vacation 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 vacation 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 vacation 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 travelers.
How far in advance should I book my Eastern Shore vacation?
Savvy travelers 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 vacation package?
With a vacation 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 vacation 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 vacation 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.
