Kid friendly Vacations in City Island 2026

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Flight and Kid friendly hotel deals in City Island

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

EVEN Hotel Brooklyn by IHG

CA $1,132

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.8/10 Excellent! (1,961 reviews)

This is my go-to hotel in Brooklyn. Very clean, great staff, comfortable bed, nice bathroom and excellent location.

Reviewed on Aug 13, 2026

NobleDEN Hotel

Manhattan

CA $2,428

per person

Oct 19 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

9.8/10 Exceptional! (1,634 reviews)

Great hotel. Great location. Fastest check-in I ever had. Staff were super helpful too. Would highly recommend.

Reviewed on Aug 13, 2026

Sound View Greenport

CA $2,033

per person

Oct 19 - Oct 26

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

8.4/10 Very good! (675 reviews)

I love this place amazing views and fun activities. I am afraid they are a bit understaffed so not everything is running smoothly. They do really really want to do a good job. Love the location so many things to do on the north fork. The Old Mill Inn is a must food is amazing and the setting beautiful plus all the food on property is very good. get a good rate and enjoy!

Reviewed on Aug 12, 2026

1 Hotel Brooklyn Bridge

CA $2,373

per person

Sep 25 - Sep 27

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Best view of manhattan NY dan Brooklyn Bridge but the only bad thing is the sound of boat every 2 hours so loud that bothers my sleep…

Reviewed on Aug 12, 2026

Omni Berkshire Place

Manhattan

CA $1,276

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (2,174 reviews)

We enjoy the Omni so much that we keep on returning year after year! Excellent location and superb staff

Reviewed on Aug 11, 2026

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5* Kid friendly holidays in City Island

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

Park Lane New York

Manhattan

CA $1,369

per person

Sep 18 - Sep 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.4/10 Very good! (1,786 reviews)

Well the first day we were there one of our rooms was not ready. We checked in at 4. We were told we would be contacted when the room was ready. Around 9 o'clock we wanted to go unpack so we went back to the hotel. The 2nd room was ready but no one called to let us know. We got to our room and it was 75 degrees, no water in the rooms. We lowered the thermostat called the front desk, they sent up a maintenance guy who emptied the water line and said it would start cooling in 20 minutes. Wake up the next morning and still 75 degrees. We again went to a manager( who was new) and she said she would check into it. Got back that afternoon it was 76 degrees so they brought up 3 fans to help cool. The last 2 days it was 77 degrees in our rooms, With 3 fans in our rooms and no one did anything. Would not recommend this hotel.

Reviewed on Aug 11, 2026

1 Hotel Brooklyn Bridge

CA $2,373

per person

Sep 25 - Sep 27

found 5 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Best view of manhattan NY dan Brooklyn Bridge but the only bad thing is the sound of boat every 2 hours so loud that bothers my sleep…

Reviewed on Aug 12, 2026

The Plaza, A Fairmont Hotel

Manhattan

CA $3,644

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,001 reviews)

Loved our stay

Reviewed on Aug 12, 2026

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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

Manhattan

CA $867

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,493 reviews)

33 Hotel, New York City, Seaport

Manhattan

CA $1,434

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (1,005 reviews)

When checking in the front desk informed me that I had $42 to spend in room order including patronage at the restaurant on site. They did not mention that the spend doesn’t include or cannot apply to gratuity. I spent $40 on the entire bill at the restaurant and the hotel only took off the portion without the gratuity. The toilet was not flushing well and toward the end of my stay the water never stopped running so I had to call the front desk at 10pm. The elevator was not working but the technician appeared to not communicate to hotel guests by just standing there. I had to carry 3 bags and took a few steps down to another elevator.

Reviewed on Aug 11, 2026

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $1,374

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (3,841 reviews)

Perfect location.

Reviewed on Aug 13, 2026

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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

Manhattan

CA $1,584

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (3,841 reviews)

Perfect location.

Reviewed on Aug 13, 2026

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,589

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (3,268 reviews)

1 Hotel Brooklyn Bridge

CA $3,357

per person

Oct 8 - Oct 12

found 18 hours ago

Roundtrip flight included

Toronto (YTZ) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Best view of manhattan NY dan Brooklyn Bridge but the only bad thing is the sound of boat every 2 hours so loud that bothers my sleep…

Reviewed on Aug 12, 2026

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See all available trips from Columbus to City Island

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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.