Eastern Shore Kid friendly Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 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

Top Kid friendly vacation packages in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Chesapeake Bay

$948

per person

Oct 21 - Oct 25

found 15 hours ago

Roundtrip flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Would definitely return in the near future. My family had fun.

Reviewed on Sep 5, 2026

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$2,259

per person

Oct 7 - Oct 14

found 8 hours ago

Roundtrip flight included

Hong Kong (HKG) to Salisbury (SBY)

8.8/10 Excellent! (1,370 reviews)

Comodidad , limpieza ,amabilidad del personal , y mucho más . Recomendado al 100%100

Reviewed on Sep 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

3 Night Kid friendly vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$623

per person

Oct 28 - Oct 31

found 15 hours ago

Roundtrip flight included

San Francisco (SFO) to Salisbury (SBY)

8.8/10 Excellent! (1,370 reviews)

Comodidad , limpieza ,amabilidad del personal , y mucho más . Recomendado al 100%100

Reviewed on Sep 5, 2026

Hyatt Regency Chesapeake Bay

$717

per person

Oct 28 - Oct 31

found 22 hours ago

Roundtrip flight included

San Francisco (SFO) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Would definitely return in the near future. My family had fun.

Reviewed on Sep 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

4 Night Kid friendly vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Comfort Suites Ocean City West

West Ocean City

$756

per person

Oct 19 - Oct 23

found 14 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Salisbury (SBY)

8.4/10 Very Good! (1,001 reviews)

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$828

per person

Oct 19 - Oct 23

found 14 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Salisbury (SBY)

9/10 Wonderful! (3,843 reviews)

The room was spacious, neat and clean. The balcony ocean front view was awesome. The sunrise was beautiful from the balcony.

Reviewed on Sep 6, 2026

Princess Royale Oceanfront Resort

North Ocean City

$1,193

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

8.8/10 Excellent! (2,727 reviews)

Very clean facility. Spacious room. Extremely convenient to many fun family things. Customer service was top notch.

Reviewed on Sep 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

How can I find the best family vacation packages in Eastern Shore?

For fam-tastic vacation packages in Eastern Shore, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Eastern Shore on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Eastern Shore cost?

You could book your amazing family trip to Eastern Shore just $623. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Eastern Shore family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Eastern Shore?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Eastern Shore family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Eastern Shore landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Eastern Shore family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Eastern Shore family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Eastern Shore Hotels

Carousel Resort Hotel & Condominiums

11700 Coastal Hwy Ocean City MD

15 min drive from Ocean City Boardwalk

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

12 min drive from Ocean City Boardwalk

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.8/10 Excellent! (2,724 reviews)

Families like: Indoor pool, game room, on the beach, bicycle rentals nearby

Travelers say...

"Very clean facility. Spacious room. Extremely convenient to many fun family things. Customer service was top notch."

Reviewed on Sep 6, 2026

Tidelands Caribbean Hotel and Suites

5th Street on the Boardwalk Ocean City Ocean City MD

3 min walk from Ocean City Boardwalk

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the pool and the clean rooms in our reviews. ...

7.2/10 Good! (1,289 reviews)

"The room was musty and had a very musty smell. The property needs to be updated and the bathroom could use some work. Parking was tight even in the overflow lot. The staff was nice."

Reviewed on Sep 7, 2026

See all 7,654 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.