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

City Island Pet-friendly Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
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Top Pet-friendly vacation packages in City Island

Price found within the past 48 hours. Click for updated prices.
  • Jan 16 - Jan 20

    33 Hotel, New York City, Seaport + Flight

    Manhattan
    4 nights
    5.0 star property
    9.0/10 - Wonderful (1,002 reviews)
    "The staff is amazing, especially Tommy and Chris. Super helpful and welcoming. Our room was spotless and beautiful in a city where things are not easily kept that way."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,363
    CA $942
    per traveller
    found 17 hours ago
    33 Hotel, New York City, Seaport
  • Jan 17 - Jan 20

    Smyth Tribeca + Flight

    Manhattan
    3 nights
    4.5 star property
    9.0/10 - Wonderful (1,003 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,356
    CA $967
    per traveller
    found 17 hours ago
    Smyth Tribeca
  • Jan 14 - Jan 17

    The Wall Street Hotel + Flight

    Manhattan
    3 nights
    5.0 star property
    9.8/10 - Exceptional (822 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $2,058
    CA $1,517
    per traveller
    found 1 day ago
    The Wall Street Hotel
  • Dec 30 - Jan 3

    Hotel Indigo Lower East Side New York by IHG + Flight

    Manhattan
    4 nights
    4.5 star property
    8.4/10 - Very good (2,189 reviews)
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - LGA • 1 stop LGA - YHM • 1 stop
    CA $2,218
    CA $1,674
    per traveller
    found 1 day ago
    Hotel Indigo Lower East Side New York by IHG
  • Dec 18 - Dec 21

    The Washington + Flight

    Manhattan
    3 nights
    3.0 star property
    7.8/10 - Good (2,428 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,511
    CA $1,186
    per traveller
    found 1 day ago
    The Washington

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 vacation package cost?

Choose from any combination of hotels, flights and car rentals, and you can be vacationing in City Island from just CA $942. 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 vacation packages promise plenty of savings for the savvy traveler. 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 vacation?

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 vacation looks like, get set to save!

What should I know before booking a City Island travel package?

Bundling your bookings into a City Island vacation package is the easiest way to organize 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 vacation 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 vacation 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 vacation 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.