---
title: "Kid friendly Vacations in Eastern Shore 2026 | Expedia.ca"
description: "Find incredible offers on Eastern Shore Kid friendly vacations! Plan your next Kid friendly trip today with Expedia."
canonical: "https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/6025644/Eastern-Shore"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-14T16:21:51Z
---

# Eastern Shore Kid friendly Vacations
![A marina with numerous boats docked at wooden piers under a clear sky.](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

## Book a Hotel + Flight or Car together to unlock savings

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## Discover the most popular places to visit in Eastern Shore

### Ocean City Boardwalk
![A boardwalk entrance with a sign reading "Boardwalk Maryland" and two lighthouse-style structures.](https://images.trvl-media.com/place/6317261/6e8df198-a349-48cd-a4bd-23a49cb2af34.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 9.0/10 (11,302 reviews)

Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6317261)

### Ocean City Beach
![A coastal cityscape with a sandy beach, ocean waves, and high-rise buildings.](https://images.trvl-media.com/place/6075473/ce713bc1-4df8-49c6-9ec2-3efae4aeab73.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 9.2/10 (10,973 reviews)

Swim in the waves of the Atlantic Ocean, relax on soft white sands or stroll by the arcades and shops on the exciting boardwalk at this family-friendly city beach.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6075473)

### Roland E. Powell Convention Center
![A stone wall with the text "Roland E. Powell Convention Center" and a landscaped area with trees and shrubs.](https://images.trvl-media.com/place/6091721/4cbad437-bd7c-4d72-a949-6d73c20436e4.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 8.0/10 (2,358 reviews)

Learn about the events happening at Roland E. Powell Convention Center during your trip to Ocean City. Stroll along the beautiful beaches or discover the beautiful sunrises in this family-friendly area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6091721)

### Jolly Roger Amusement Park
![A carousel, a large statue, and a building with a neon sign.](https://images.trvl-media.com/place/6166993/06b1cc42-376a-4f0a-991b-a42b73513533.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 8.2/10 (3,806 reviews)

Bring your family to Jolly Roger Amusement Park and have a fun-filled day at this theme park in Ocean City. Amble around this family-friendly area's seaside, or seek out the golf courses.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6166993)

### Inlet Park
![A wooden boardwalk by a body of water with binoculars and a bench.](https://images.trvl-media.com/place/6289842/6cdce661-d3b6-4fc6-a501-dadeb007f48e.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 8.6/10 (1,457 reviews)

Explore the lovely green spaces of Inlet Park and enjoy the golf courses in Ocean City. Stroll along the beautiful beaches or discover the area's beautiful sunrises.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6289842)

### Jolly Roger at the Pier
![A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.](https://images.trvl-media.com/place/553248621592457169/7d6ad9b9-fb22-4437-899b-facd1a03b791.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 8.4/10 (2,874 reviews)

The old classics get a new spin at this waterfront fun park, which has an exciting collection of wild rides, high-octane roller coasters and traditional amusements.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=553248621592457169)

### Salisbury University

Rating: 8.4/10 (452 reviews)

Take a campus tour or just explore the area of Salisbury University, during your trip to Salisbury. While you're in the area, stroll along the beautiful beaches.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=family%5Ffriendly&regionId=6172466)

### What to do in Eastern Shore

![Funfull Family Package Delmarva](https://mediaim.expedia.com/localexpert/51480856/85a958b9-64ed-41fb-aa09-df5c20361035.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Funfull Family Package Delmarva](https://www.expedia.ca/things-to-do/a.a51480856.activity-details?rid=6025644)

CA $987

per adult

0% of travellers recommend

[See all activities in Eastern Shore](https://www.expedia.ca/things-to-do/search?rid=6025644)

## Top Kid friendly Eastern Shore Hotels

### [Holiday Inn Express Annapolis East-Kent Island by IHG](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Two Adirondack chairs facing a calm body of water with a clear sky above.](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1020 Kent Narrows Rd, Grasonville, MD, 21638, US
- Location: 47.8 km from Eastern Shore
- Star rating: 2.5/5
- Guest rating: 9.2/10 (Wonderful, 1002 reviews)
- Price: CA $136, CA $150 total, includes taxes & fees, Dec 13 - Dec 14, for Top Kid friendly Eastern Shore Hotels
- Review: Helpful staff, nice location on the river

### [Grand Hotel Ocean City Oceanfront](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information)

![A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 2100 N Baltimore Ave, Ocean City, MD, 21842, US
- Location: 76.4 km from Eastern Shore
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 4008 reviews)
- Price: CA $76, CA $85 total, includes taxes & fees, Nov 18 - Nov 19, for Top Kid friendly Eastern Shore Hotels
- Review: Wonderful balcony/beach view! In-room internet was so-so. Comfy bed, OK shower

### [Hampton Inn & Suites Ocean City/Bayfront-Convention Center](https://www.expedia.ca/Ocean-City-Hotels-Hampton-Inn-Suites-Ocean-City.h5121459.Hotel-Information)

![A pool area with lounge chairs, a hot tub, and a view of the ocean.](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/1116dd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 4301 Coastal Hwy, Ocean City, MD, 21842, US
- Location: 75.8 km from Eastern Shore
- Star rating: 2.5/5
- Guest rating: 8.8/10 (Excellent, 1000 reviews)
- Price: CA $84, CA $94 total, includes taxes & fees, Dec 7 - Dec 8, for Top Kid friendly Eastern Shore Hotels

### [Cambria Hotel Ocean City - Bayfront](https://www.expedia.ca/Ocean-City-Hotels-Cambria-Hotel-Ocean-City-Bayfront.h46182729.Hotel-Information)

![A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.](https://images.trvl-media.com/lodging/47000000/46190000/46182800/46182729/4f97c88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 13 SAINT LOUIS AVE, Ocean City, MD, 21842, US
- Location: 76.4 km from Eastern Shore
- Star rating: 3/5
- Guest rating: 9.2/10 (Wonderful, 1000 reviews)
- Price: CA $97, CA $130 total, includes taxes & fees, Dec 7 - Dec 8, for Top Kid friendly Eastern Shore Hotels
- Review: The room was gorgeous

### [St Michaels Inn](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ee980eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1228 S Talbot Street, St. Michaels, MD, 21663, US
- Location: 32.5 km from Eastern Shore
- Star rating: 2.5/5
- Guest rating: 8/10 (Very good, 1003 reviews)
- Price: CA $112, CA $123 total, includes taxes & fees, Dec 3 - Dec 4, for Top Kid friendly Eastern Shore Hotels

### [DoubleTree by Hilton Ocean City Oceanfront](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information)

![A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/a68045c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 3301 Atlantic Ave, Ocean City, MD, 21842, US
- Location: 76.2 km from Eastern Shore
- Star rating: 4/5
- Guest rating: 9/10 (Wonderful, 1003 reviews)
- Price: CA $116, CA $130 total, includes taxes & fees, Nov 22 - Nov 23, for Top Kid friendly Eastern Shore Hotels

### [Best Western Kent Narrows Inn](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/e2a3e8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 3101 Main Street, Grasonville, MD, 21638, US
- Location: 47.7 km from Eastern Shore
- Star rating: 2.5/5
- Guest rating: 8/10 (Very good, 1002 reviews)
- Price: CA $128, CA $142 total, includes taxes & fees, Nov 24 - Nov 25, for Top Kid friendly Eastern Shore Hotels
- Review: All the rooms have an outside entry, very noisy (highway) if you're on the backside.

### [Quality Inn Grasonville near Kent Island](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information)

![A spacious lobby with a staircase, a reception desk, and a dining area.](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 101 Vfw Ave, Grasonville, MD, 21638, US
- Location: 45.1 km from Eastern Shore
- Star rating: 2.5/5
- Guest rating: 7.8/10 (Good, 1004 reviews)
- Price: CA $118, CA $130 total, includes taxes & fees, Dec 13 - Dec 14, for Top Kid friendly Eastern Shore Hotels

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.

[See all properties in Eastern Shore](https://www.expedia.ca/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&regionId=6025644&adults=2&travelerType=family%5Ffriendly&sort=RECOMMENDED&openPlayBack=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.

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- [Flights from Preston](https://www.expedia.ca/lp/flights/3000440824/flights-from-preston)
- [Flights from Toronto (YYZ) to Baltimore (BWI)](https://www.expedia.ca/lp/flights/yyz/bwi/toronto-to-baltimore)
- [Flights from Calgary (YYC) to Baltimore (BWI)](https://www.expedia.ca/lp/flights/yyc/bwi/calgary-to-baltimore)
- [Flights from Montreal (YUL) to Cambridge (CGE)](https://www.expedia.ca/lp/flights/yul/cge/montreal-to-cambridge)
- [Flights from Albany (ALB) to Cambridge (CGE)](https://www.expedia.ca/lp/flights/alb/cge/albany-to-cambridge)
- [Flights from Hagerstown (HGR) to Cambridge (CGE)](https://www.expedia.ca/lp/flights/hgr/cge/hagerstown-to-cambridge)
- [Flights from Allentown (ABE) to Easton (ESN)](https://www.expedia.ca/lp/flights/abe/esn/allentown-to-easton)
- [Flights from Cincinnati (CVG) to Easton (ESN)](https://www.expedia.ca/lp/flights/cvg/esn/cincinnati-to-easton)
- [Flights from Toronto (YYZ) to Cambridge (CGE)](https://www.expedia.ca/lp/flights/yyz/cge/toronto-to-cambridge)
- [Flights to Baltimore](https://www.expedia.ca/Cheap-Flights-To-Baltimore.d178235.Travel-Guide-Flights)
- [Flights to Maryland](https://www.expedia.ca/Destinations-In-Maryland.d222.Flight-Destinations)
- [Flights to Kent Island](https://www.expedia.ca/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)
- [Flights to Washington](https://www.expedia.ca/Cheap-Flights-To-Washington.d178318.Travel-Guide-Flights)
- [Flights to Eastern Shore](https://www.expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)
- [Flights from Winnipeg (YWG) to Baltimore (BWI)](https://www.expedia.ca/lp/flights/ywg/bwi/winnipeg-to-baltimore)
- [Flights to St. Michaels](https://www.expedia.ca/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)
- [Flights to Cambridge](https://www.expedia.ca/Cheap-Flights-To-Cambridge.d6608.Travel-Guide-Flights)
- [Flights from Los Angeles (LAX) to Easton (ESN)](https://www.expedia.ca/lp/flights/lax/esn/los-angeles-to-easton)
- [Flights from Washington (DCA) to Easton (ESN)](https://www.expedia.ca/lp/flights/dca/esn/washington-to-easton)
- [Visit Annapolis](https://www.expedia.ca/Annapolis.dx6034082)
- [Visit Cambridge](https://www.expedia.ca/Cambridge.dx6608)
- [Visit Eastern Shore](https://www.expedia.ca/Eastern-Shore.dx6025644)
- [Golf Vacation Packages Maryland](https://www.expedia.ca/lp/theme-vacations/golf-vacations/222/Maryland)
- [All inclusive Vacation Packages Washington](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/178318/Washington)
- [Visit Maryland](https://www.expedia.ca/Maryland.dx222)
- [All inclusive Vacation Packages Maryland](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/222/Maryland)
- [Washington Vacations](https://www.expedia.ca/Washington.d178318.Destination-Travel-Guides)
- [Visit Easton](https://www.expedia.ca/Easton.dx7120)
- [Visit Downtown Cambridge](https://www.expedia.ca/Cambridge-Downtown-Cambridge.dx553248635149747882)
- [Long Wharf Park](https://www.expedia.ca/Long-Wharf-Park-Cambridge.d6286116.Vacation-Attraction)
- [Avis Rental Cars in Easton](https://www.expedia.ca/Avis-Car-Rentals-In-Easton.d7120-c41.Car-Rental-Guide-Suppliers)
- [Rent A Wreck Rental Cars in Eastern Shore](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Eastern-Shore.d6025644-c33.Car-Rental-Guide-Suppliers)
- [Things to do in Maryland](https://www.expedia.ca/Things-To-Do-In-Maryland.d222.Travel-Guide-Activities)
- [Things to do in Annapolis](https://www.expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)

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