Title: Kid friendly Vacations in Eastern Shore 2026 | Expedia.ca

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# Eastern Shore Kid friendly Vacations

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## Flight and Kid friendly hotel deals in Eastern Shore

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

![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency Chesapeake Bay

CA $1,006

per person

Mar 12 - Mar 16

found 24 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Salisbury (SBY)

8.8/10 Excellent! (1,000 reviews)

Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.

Reviewed on Dec 5, 2025

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Kid friendly holidays in Eastern Shore

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

![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Ocean City Oceanfront

Downtown Ocean City

CA $773

per person

Mar 12 - Mar 16

found 24 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Salisbury (SBY)

9/10 Wonderful! (3,316 reviews)

Very clean and nice. Its a hotel and i only stayed overnight for work but it was very nice

Reviewed on Dec 17, 2025

![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency Chesapeake Bay

CA $1,006

per person

Mar 12 - Mar 16

found 24 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Salisbury (SBY)

8.8/10 Excellent! (1,000 reviews)

Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.

Reviewed on Dec 5, 2025

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ILG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Plan the perfect family-friendly vacation in Eastern Shore with Expedia

####  What are some benefits of booking a family-friendly vacation? 

Whether it's luxurious or cheap, family vacations in Eastern Shore are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. 
  
####  How can I find the best family-friendly vacations? 

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Eastern Shore. 

####  Are there cheap family vacations to Eastern Shore? 

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. 

####  When should I book family-friendly vacation packages? 

The right time to book family-friendly vacation packages in Eastern Shore depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. 

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

Yes, you'll find plenty of all-inclusive family vacation packages for Eastern Shore. To see what's available, just select the all-inclusive filter on your search.

####  How can I book the best family activity vacation? 

If you're looking to make the most out of the available activities in Eastern Shore, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Eastern Shore or something a bit more relaxed.

####  Can I find luxury family vacations in Eastern Shore? 

If you're looking for a luxury family vacation to Eastern Shore, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. 

####  How can I search for family vacation deals? 

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Eastern Shore. 

####  Can I book a family vacation package that is fully refundable? 

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Eastern Shore are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

####  Why should I book my family trip with Expedia? 

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

## Kid friendly Hotels in Eastern Shore

![Carousel Resort Hotel & Condominiums](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/72fa8dcb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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! (1,401 reviews)

10 guests booked between 2 rooms and only 2 washcloths and towels in each room, tub had dirt in it, other than that no issues

Reviewed on Dec 15, 2025

[](https://expedia.ca/Ocean-City-Hotels-Carousel-Resort-Hotel-Condominiums.h16138.Hotel-Information)

![Princess Royale Oceanfront Resort](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/b0fe2b94_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 ...

8.6/10 Excellent! (2,298 reviews)

The entire stay was amazing! We will definitely be booking a future vacation.

Reviewed on Dec 12, 2025

[](https://expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information)

![Tidelands Caribbean Hotel and Suites](https://images.trvl-media.com/lodging/2000000/1510000/1503100/1503015/36d7c3e9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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, free parking, and 2 outdoor pools. Our guests praise the pool and the clean rooms in our reviews. ...

7/10 Good! (1,202 reviews)

very nice

Reviewed on Dec 15, 2025

[](https://expedia.ca/Ocean-City-Hotels-Tidelands-Caribbean-Hotel-And-Suites.h1503015.Hotel-Information)

[See all 7,555 properties in Eastern Shore](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6025644)

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.

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## More Vacations Ideas

[Flights to Eastern Shore

](https://expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[

Eastern Shore Hotels

](https://expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[

Eastern Shore Vacation Rentals

](https://expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[

Eastern Shore Car Rentals

](https://expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[

Eastern Shore Vacations

](https://expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides)[

Things to do in Eastern Shore

](https://expedia.ca/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)

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