City Island Kid friendly Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and Kid friendly hotel deals in City Island

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

Radio Hotel

Manhattan
CA $689
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,506 reviews)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
CA $1,672
per person
Oct 9 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
Positives: Location Clean Well maintained Helpful staff Negatives: Can have more vegetarian options in breakfast Rooms are a little too small

Reviewed on Aug 7, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
CA $1,509
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
1 Hotel Central Park

1 Hotel Central Park

Manhattan
CA $3,096
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Lotte New York Palace

Lotte New York Palace

Manhattan
CA $1,848
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,159 reviews)
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5* Kid friendly holidays in City Island

Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $3,009
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
The suite I got was unbelievable , best view ever from Brooklyn bridge . The service , the staff , everything perfect . Just the roof & pool and the is nothing crazy, honest , is very little , . Few chairs lit bit disappointed from the one in Miami . …

Reviewed on Aug 6, 2026

1 Hotel Central Park

1 Hotel Central Park

Manhattan
CA $3,096
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
The Wall Street Hotel

The Wall Street Hotel

Manhattan
CA $3,052
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (726 reviews)
Don't see what you're looking for?
See all available trips from Columbus to City Island
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3 Night Kid friendly holidays in City Island

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

Radio Hotel

Manhattan
CA $689
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,506 reviews)
The Wall Street Hotel

The Wall Street Hotel

Manhattan
CA $1,790
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (726 reviews)
Hotel AKA NoMad

Hotel AKA NoMad

Manhattan
CA $1,046
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Don't see what you're looking for?
See all available trips from Columbus to City Island
View all trips

4 Night Kid friendly holidays in City Island

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
CA $1,509
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
CA $1,672
per person
Oct 9 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
Positives: Location Clean Well maintained Helpful staff Negatives: Can have more vegetarian options in breakfast Rooms are a little too small

Reviewed on Aug 7, 2026

The Wall Street Hotel

The Wall Street Hotel

Manhattan
CA $2,329
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (726 reviews)
Don't see what you're looking for?
See all available trips from Columbus to City Island
View all trips

Plan the perfect family-friendly vacation in City Island with Expedia

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

Whether it's luxurious or cheap, family vacations in City Island 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 City Island.

Are there cheap family vacations to City Island?

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 City Island 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 City Island?

Yes, you'll find plenty of all-inclusive family vacation packages for City Island. 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 City Island, 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 City Island or something a bit more relaxed.

Can I find luxury family vacations in City Island?

If you're looking for a luxury family vacation to City Island, 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 City Island.

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 City Island 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.

Things to do

Edge Observation Deck at Hudson Yards

Edge Immersive Observation Deck Ticket

CA $61
per adult
94% of travellers recommend
Edge Immersive Observation Deck Ticket
American Dream: SEA LIFE New Jersey Aquarium

American Dream: SEA LIFE New Jersey Aquarium

CA $53
per traveller
88% of travellers recommend
American Dream: SEA LIFE New Jersey Aquarium
Statue of Liberty & Ellis Island Sunset Cruise

Statue of Liberty & Ellis Island Sunset Cruise

CA $49
per adult
78% of travellers recommend
Statue of Liberty & Ellis Island Sunset Cruise
See all activities in City Island

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.