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

City Island Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to €900 when you book a flight and hotel together*
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    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

Top Luxury holiday packages in City Island

Price found within the past 48 hours. Click for updated prices.
  • 26 Dec - 31 Dec

    Belvilla District 6 Residences, Battery Park, Financial District + Flight

    Manhattan
    5 nights
    2.0 star property
    8.8/10 - Excellent (711 reviews)
    "Sonder "
    Reviewed January 26, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • 1 stop
    €2,378
    €1,743
    per traveller
    found 1 day ago
    Belvilla District 6 Residences, Battery Park, Financial District
  • 26 Dec - 31 Dec

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (4,165 reviews)
    "Clean, staff was lovely. Easy access to Broadway shows."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    €4,066
    €2,669
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • 26 Dec - 31 Dec

    Hotel Beacon + Flight

    Manhattan
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,550 reviews)
    "5 stars in every way."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • 1 stop
    €3,343
    €2,351
    per traveller
    found 1 day ago
    Hotel Beacon
  • 20 Jan - 24 Jan

    The St. Regis New York + Flight

    Manhattan
    4 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    €5,498
    €4,074
    per traveller
    found 1 day ago
    The St. Regis New York
  • 26 Dec - 31 Dec

    PUBLIC, an Ian Schrager hotel + Flight

    Manhattan
    5 nights
    4.0 star property
    8.8/10 - Excellent (4,108 reviews)
    "Lovely hotel. The urban garden in front is a lovely feature in an otherwise somewhat scruffy area. Intelligent and aesthetically pleasing interior design that steps away from typical hotel room design. But the thumping techno — one night until 2:30 a.m. in the bar below me — was beyond the pale. Totally inconsiderate and unacceptable. It is the hotel’s responsibility to provide a tranquil sleeping environment for overnight guests. On this, it failed."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    €2,368
    €1,920
    per traveller
    found 1 day ago
    PUBLIC, an Ian Schrager hotel

Discover the most popular places to visit in City Island

What to do 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 €1,743. 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.