Eastern Shore Kid friendly Vacations

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Top Kid friendly vacation packages in Eastern Shore

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

$1,106
per person
Oct 15 - Oct 18
found 5 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

Hilton Ocean City Oceanfront Suites

Midtown Ocean City
$1,169
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.8/10 Excellent! (1,377 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

Hilton Ocean City Oceanfront Suites

Midtown Ocean City
$623
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Salisbury (SBY)
8.8/10 Excellent! (1,377 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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

$1,106
per person
Oct 15 - Oct 18
found 5 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

Comfort Suites Ocean City West

West Ocean City
$688
per person
Oct 16 - Oct 20
found 9 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.4/10 Very Good! (1,001 reviews)
Our experience at this Comfort Suites was not great. While our room was clean, during our two-night stay, our room was never serviced or cleaned. We went down for breakfast around 8:00 a.m., and there were no eggs and only a few sausage patties available. My husband and I ended up walking over to OC Diner, which, by the way, was great! The pool area was very crowded, including several guests with dogs. One adult male even had his feet up on top of a table while relaxing. I also was not too happy with the number of animals around the property. I saw a few children taking their dogs to use the bathroom right in front of the entrance. On a positive note, the location was convenient and close to the beach, shopping, and restaurants. However, overall, this would not be my choice for a second stay.

Reviewed on Sep 8, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

Downtown Ocean City
$828
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Salisbury (SBY)
9/10 Wonderful! (3,843 reviews)
Unfortunately, our experience at this hotel was extremely disappointing, particularly during check-in. When we were first assigned a room and opened the door, there was already a family staying inside. They were understandably shocked to see us entering their room, and one of the occupants was partially undressed. I was traveling with my three-year-old daughter, so this was especially disturbing and completely unacceptable. Beyond the embarrassment, this was also a serious privacy and security concern. We went back to the front desk and were assigned a second room. Once inside, we discovered that the connecting door leading to the neighboring room would not properly lock, which made us feel unsafe and uncomfortable staying there. We were then moved to a THIRD room, only to find that it had a significant number of bugs inside. At that point, after being sent to three different rooms with three separate major problems, we expected management to acknowledge how badly the situation had been handled and make some meaningful effort to accommodate us or make things right. Unfortunately, that never happened. Checkout was not particularly good either, but the check-in experience was by far the worst part of our stay. Being given access to an occupied room, exposing my three-year-old to someone who was partially undressed, then being moved to an unsecured room, followed by a room with bugs, is far beyond what any paying guest should reasonably expect.

Reviewed on Sep 8, 2026

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

North Ocean City
$1,382
per person
Oct 9 - Oct 13
found 8 hours ago
Roundtrip non-stop flight included
PBI (PBI) to Salisbury (SBY)
8.8/10 Excellent! (2,727 reviews)
The staff was very friendly and helpful throughout our stay. Everything was well organized, and we really enjoyed our time here. It was a great place to relax and spend quality time with family.

Reviewed on Sep 8, 2026

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FAQs: family vacation packages in Eastern Shore

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

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! (1,466 reviews)

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

Travelers say...
"100%"

Reviewed on Sep 8, 2026

Carousel Resort Hotel & Condominiums
Princess Royale Oceanfront Resort

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! (2,731 reviews)

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

Travelers say...
"The staff was very friendly and helpful throughout our stay. Everything was well organized, and we really enjoyed our time here. It was a great place to relax and spend quality time with family."

Reviewed on Sep 8, 2026

Princess Royale Oceanfront Resort
Tidelands Caribbean Hotel and Suites

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! (1,291 reviews)
"Hotel needs major upgrades. Very dirty. Don’t waste your money."

Reviewed on Sep 7, 2026

Tidelands Caribbean Hotel and Suites
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.

More vacations you might like

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