Save up to €900 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Discover the most popular places to visit in Eastern Shore
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.
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.
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.
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.
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.
Northside Park
8.2/10 (1,682 reviews)
Ocean City's largest park spans 58 acres with sports fields, playgrounds, and piers extending into Assawoman Bay. Stroll along scenic waterfront paths or attend popular summer events like Sundaes in the Park.
Top Kid friendly Eastern Shore Hotels
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
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.
How can I find the best family-friendly holidays in Eastern Shore?
At Expedia, it’s super-easy to find family-friendly holidays in Eastern Shore in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.
Are there any cheap Eastern Shore family holidays?
Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Eastern Shore family getaways start at . Prices and availability are subject to change and additional terms may apply.
Can I book an all-inclusive Eastern Shore family holiday package?
All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Eastern Shore and book the whole package in just a few clicks.
How can I book the best family activity holiday in Eastern Shore?
Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.
Can I find luxury family holidays in Eastern Shore?
To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Eastern Shore by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.
How can I search for Eastern Shore family holiday deals?
Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Eastern Shore family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.
Can I book a Eastern Shore family vacation package with free cancellation and/or flexible dates?
Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.
Why should I book my Eastern Shore family trip with Expedia?
Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Eastern Shore in no time.