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

City Island Honeymoon 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*
  • 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

Top Honeymoon vacation packages in City Island

Price found within the past 48 hours. Click for updated prices.
  • Jan 22 - Jan 24

    Hotel Seville Nomad, in the Unbound Collection by Hyatt + Flight

    Manhattan
    2 nights
    4.5 star property
    8.8/10 - Excellent (1,574 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $976
    CA $581
    per traveller
    found 1 day ago
    Hotel Seville Nomad, in the Unbound Collection by Hyatt
  • Jan 22 - Jan 24

    The St. Regis New York + Flight

    Manhattan
    2 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
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,690
    CA $1,323
    per traveller
    found 1 day ago
    The St. Regis New York
  • Jan 7 - Jan 10

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - EWR • 1 stop LGA - YHM • 1 stop
    CA $2,227
    CA $1,249
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 22 - Jan 24

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.0/10 - Wonderful (3,453 reviews)
    "The staff was friendly, and helpful. Our room was clean, but very small. Being next to the elevator was not the best as you can hear everything. The location of the hotel is excellent. No parking on site, but there is a parking garage a couple blocks away."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,166
    CA $664
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • Jan 22 - Jan 24

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.2/10 - Wonderful (4,180 reviews)
    "This is a very nice and upscale hotel. It’s close to so many things - great location, very clean, staff was super friendly and I feel the price was great!"
    Reviewed November 11, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,077
    CA $616
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square

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 $581. 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.