Eastern Shore Kid friendly Vacations 2026

Top Kid friendly vacation packages in Eastern Shore

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

Hyatt Regency Chesapeake Bay

$1,106

per person

Oct 15 - Oct 18

found 2 hours ago

Roundtrip flight included

Philadelphia (PHL) 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 16 hours ago

Roundtrip flight included

Hong Kong (HKG) to Salisbury (SBY)

8.8/10 Excellent! (1,370 reviews)

This visit highlights cleanliness. For example, the family room lamps had 2 inches of dust on the rod design. Although, our stay was 5 days, we didn’t ask to have our room cleaned until the 4 th day. The sheets were not replaced until I requested that the cleaning person return to replace them. It was obvious to us the sheets needed to be replaced. Mopping the kitchenette wasn’t thoroughly done. No bath tissue was refilled. More attention to details even in a rush is needed.

Reviewed on Sep 7, 2026

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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 24 hours ago

Roundtrip flight included

San Francisco (SFO) to Salisbury (SBY)

8.8/10 Excellent! (1,370 reviews)

Reviewed on Sep 7, 2026

Hyatt Regency Chesapeake Bay

$1,106

per person

Oct 15 - Oct 18

found 2 hours ago

Roundtrip flight included

Philadelphia (PHL) 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

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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

$688

per person

Oct 16 - Oct 20

found 6 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

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

I was very happy with the hotel. I'm coming back again.

Reviewed on Sep 7, 2026

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$828

per person

Oct 19 - Oct 23

found 23 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Salisbury (SBY)

9/10 Wonderful! (3,843 reviews)

We absolutely loved the Grand. It was our first time staying. Hotel is like a resort. A choice of a few restaurants, indoor and outdoor pools, a lot of shopping, pool tables and more. The only negatives is the service at the pool bar and the indoor grill is terrible. Husband and I waited 15 minutes for drinks every time. We will definitely be back though. Hopefully the service next time is better.

Reviewed on Sep 7, 2026

Princess Royale Oceanfront Resort

North Ocean City

$1,382

per person

Oct 9 - Oct 13

found 4 hours ago

Roundtrip non-stop flight included

PBI (PBI) to Salisbury (SBY)

8.8/10 Excellent! (2,727 reviews)

Hay ratones,y la basura de afuera no la botan diaria

Reviewed on Sep 7, 2026

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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. ...

7.8/10 Good! (1,462 reviews)

Families like: Outdoor pool, playground, game room, on the beach

Travelers say...

"Great price! Great location! The staff was friendly and very helpful."

Reviewed on Sep 7, 2026

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! (2,730 reviews)

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

Travelers say...

"Hay ratones,y la basura de afuera no la botan diaria"

Reviewed on Sep 7, 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! (1,290 reviews)

"The bathroom door didn’t lock, the tub didn’t drain, and the main door didn’t lock. We stayed Friday thru Monday. There was nobody at the front desk on Saturday all day (never got fresh towels). There is no cafe onsite. The pool didn’t open until 10am. The phone in the room didn’t work. The staff ..."

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.