City Island Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

City Island Holiday

Our pick of the best City Island Hotel Deals

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is NZ$398 per night from 10 Aug to 11 Aug
NZ$398
10 Aug - 11 Aug
includes taxes & fees
7.4/10 Good! (4,077 reviews)
"its good"

Reviewed on 3 Aug. 2025

Sheraton New York Times Square Hotel
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street, at Grand Central Terminal, New York, NY
Fully refundableReserve now, pay when you stay
The price is NZ$407 per night from 17 Aug to 18 Aug
NZ$407
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (5,873 reviews)
"good"

Reviewed on 3 Aug. 2025

Hyatt Grand Central New York
Hotel St. James

Hotel St. James

2.5 out of 5
109 W. 45TH ST., New York, NY
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (6,186 reviews)
"Such a friendly, classic place to stay in NYC"

Reviewed on 1 Aug. 2025

Get rates
Hotel St. James
See all 10,694 properties in City Island
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.

Discover the most popular places to visit in City Island

Times Square

Times Square

The electric atmosphere of the New York’s busiest square will leave your head spinning, an essential experience for all visitors.

Times Square
Central Park which includes a park, flowers and a pond

Central Park

Sit back and relax in this iconic oasis of calm right in the heart of Manhattan’s concrete jungle.

Central Park
Ed Sullivan Theater featuring a city and signage as well as a large group of people

Broadway

Visit the dazzling theater district of one of the world’s most exciting cities. Enjoy the shopping, dining and street entertainment as well.

Broadway

What to do in City Island

New York’s Best Skyline View, Top of the Rock at Rockefeller Center

Top of the Rock Observation Deck

NZ$75
per adult
88% of travellers recommend
Top of the Rock Observation Deck
American Museum of Natural History Tickets

American Museum of Natural History Tickets

NZ$45
per adult
78% of travellers recommend
American Museum of Natural History Tickets
Circle Line: Best of New York Cruise – All Around Manhattan

Circle Line: Best of New York Cruise – All Around Manhattan

NZ$69
per adult
94% of travellers recommend
Circle Line: Best of New York Cruise – All Around Manhattan
See all activities in City Island

Frequently asked questions

How much does a City Island holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in City Island from just . And the more you bundle, the more cash you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to City Island?
Our City Island holiday packages promise plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and rental cars into an affordable package. But bargain prices are just the beginning of your next awesome adventure. Book with Expedia and you'll have more than 550 airlines and 1 000 000 hotel options worldwide to pick from. Whatever your budget or style, there's a package that's perfect for you.
How far in advance should I book my City Island holiday?
While not all air carriers advertise tickets early, you can normally start comparing international airfares on Expedia up to 12 months in advance. This is when you'll bag some incredible bargains. If you're booking at the last minute, you could still be in luck. Low prices sometimes emerge only weeks prior to departure.
What does an Expedia City Island travel package include?
It's up to you! You can select from a range of City Island packages, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your dream City Island holiday looks like, get set to save!
What should I know before booking a City Island travel package?
Bundling your bookings into a City Island holiday package is the easiest way to organise your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a City Island Expedia holiday package?
Yes, and with more than 550 airlines to select from worldwide, you're not short on choice. Have a look through the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my City Island holiday package?
Yes, you can. We totally understand that even the best-laid plans can fail, so we're happy to help if you need to make changes to your City Island holiday package. You may be able to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.