A river winding through a densely populated residential area with numerous houses and docks along the water.

City Island Holidays from NZ$906

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest City Island Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 20 Oct - 22 Oct

    Hotel St. James + Flight

    Manhattan
    2 nights
    3.0 star property
    8.8/10 - Excellent (7,738 reviews)
    "Helpful and kind staff. No fridge in the room, very small elevators, toilet broke twice for no reason, construction started in the hallway outside our room at 8:30 am and was very disruptive especially since the hallways are so narrow and they had ladders and equipment in the way."
    Reviewed August 5, 2026
    Return Boston (BOS) - New York (JFK)
    BOS - JFKDirect LGA - BOSDirect
    Save 100% on your flight
    NZ$1,279
    NZ$906
    per traveller
    found 1 day ago
    Hotel St. James
  • 20 Oct - 22 Oct

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.2/10 - Wonderful (3,849 reviews)
    Return Boston (BOS) - New York (JFK)
    BOS - JFKDirect LGA - BOSDirect
    Save 100% on your flight
    NZ$1,908
    NZ$1,233
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • 20 Oct - 22 Oct

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.0/10 - Wonderful (3,269 reviews)
    "The only issue with the room...of the bathroom light was on, you could see the person in the shower...the full silhouette at least. Breakfast was great as it was included with our rate. The cost was a tad higher than I wanted to pay at over $500 for 1 night, but the experience and location were wonderful."
    Reviewed August 5, 2026
    Return Boston (BOS) - New York (JFK)
    BOS - JFKDirect LGA - BOSDirect
    Save 100% on your flight
    NZ$1,862
    NZ$1,207
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • 20 Oct - 22 Oct

    Hotel Beacon + Flight

    Manhattan
    2 nights
    4.0 star property
    9.4/10 - Exceptional (1,498 reviews)
    "Staff was absolutely amazing. So warm, friendly, and helpful. Room was very nice, clean, comfortable. Wouldn’t hesitate to stay there again."
    Reviewed August 2, 2026
    Return Boston (BOS) - New York (JFK)
    BOS - JFKDirect LGA - BOSDirect
    Save 100% on your flight
    NZ$1,687
    NZ$1,106
    per traveller
    found 1 day ago
    Hotel Beacon
  • 20 Oct - 22 Oct

    OYO Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    6.8/10 - (2,054 reviews)
    "The room was horrible !! The bed was so thin and the blinds were terrible all beat up with holes. The noise from the street was so loud. The bathroom was literally like showering on the street!!! I would never stay there and we left during the night!!! Horrible stay! Do not waste any money here! They cheated some few per day that I’m trying to dispute. !!! We didn’t charge anything we didn’t even stay for 24 hours"
    Reviewed August 4, 2026
    Return Boston (BOS) - New York (JFK)
    BOS - JFKDirect LGA - BOSDirect
    Save 100% on your flight
    NZ$1,293
    NZ$936
    per traveller
    found 1 day ago
    OYO Times Square

What to do in City Island

City Island Hotel Deals

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.

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 NZ$906. 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.