City Island Kid friendly Vacations

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Flight and Kid friendly hotel deals in City Island

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

The Evelyn Hotel

Manhattan
Save 100% on your flight
CA $1,663
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,368 reviews)
Located outside of midtown, this location is good for those looking to get away from the crowds of midtown. The front desk and restaurants are all on one level meaning those that are stairs challenged will make out fine.

Reviewed on Sep 28, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
CA $3,495
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (702 reviews)
Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
CA $1,715
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,230 reviews)
Everything

Reviewed on Sep 28, 2026

1 Hotel Central Park

1 Hotel Central Park

Manhattan
Save 100% on your flight
CA $3,142
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
The High Line Hotel

The High Line Hotel

Manhattan
Save 100% on your flight
CA $2,167
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
There are hotels that have "shabby chic" and there are hotels that, like this one, are just neglectfully shabby. What a disappointment for the amount of money spent on the room... that there is no real lobby is a structural choice they made, which is sad. That they refuse to turn the coffee station into a bar at night (when the outdoor bar is closed due to weather) is a poor choice, like they don't care about the guests... that they leave a window air-condition in the window when it's cold and have a tape keep the plastic together--and the outside noise and cold air come into the first-floor room, is a choice, as well. The curtains could use rehanging, the towels are so frayed that they tear, and despite claiming it's a "deluxe" room, there is neither light not end-table on one side (and you have to jump over the bed to get to your side of the bed (when coupled).

Reviewed on Sep 27, 2026

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5* Kid friendly holidays in City Island

Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel

Loews Regency New York Hotel

Manhattan
Save 100% on your flight
CA $2,644
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
CA $3,495
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (702 reviews)
1 Hotel Central Park

1 Hotel Central Park

Manhattan
Save 100% on your flight
CA $3,142
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
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3 Night Kid friendly holidays in City Island

Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
CA $1,715
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,230 reviews)
Everything

Reviewed on Sep 28, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
CA $2,252
per person
Nov 14 - Nov 17
just found
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9.2/10 Wonderful! (702 reviews)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
CA $2,376
per person
Nov 14 - Nov 17
just found
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
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4 Night Kid friendly holidays in City Island

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

Night Hotel Broadway

Manhattan
Save 100% on your flight
CA $1,472
per person
Dec 3 - Dec 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,693 reviews)
Staff was great room was slightly nasty but not unbearable I would go and stay again for a last minute change greatful just wish was more clean but the staff was awesome and the cleaning ladies were amazing they help as much as they possibly can I just think it’s an old outdated place and needs a lil makeover!

Reviewed on Sep 28, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
CA $2,723
per person
Nov 8 - Nov 12
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
Save 100% on your flight
CA $1,939
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,000 reviews)
Perfect location and wonderful staff.

Reviewed on Sep 28, 2026

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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

Tyrannosaurs rex skeleton in the American Museum of Natural History in New York

American Museum of Natural History Tickets

CA $57
per adult
82% of travellers recommend
American Museum of Natural History Tickets
Edge Immersive Observation Deck Ticket

Edge Immersive Observation Deck Ticket

CA $60
per adult
96% of travellers recommend
Edge Immersive Observation Deck Ticket
Statue of Liberty & Ellis Island Sunset Cruise

Statue of Liberty & Ellis Island Sunset Cruise

CA $45
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.