City Island Vacation Packages

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 City Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,714, price is now CA $993 per person
CA $993
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,514, price is now CA $1,371 per person
CA $1,371
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 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 on Nov 6, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was CA $3,716, price is now CA $2,105 per person
CA $2,105
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,292, price is now CA $1,422 per person
CA $1,422
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

LGA AIRPORT

LGA AIRPORT

2 out of 5
Queens
Price was CA $1,788, price is now CA $1,126 per person
CA $1,126
per person
Jan 15 - Jan 19
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.

Reviewed on Dec 24, 2025

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City Island Hotel Deals

ROW NYC

ROW NYC

4 out of 5
700 8th Avenue New York NY
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Nov 22 to Nov 23
CA $242
CA $349 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (3,152 reviews)
"Hotel is midtown, close to the subway, broadway, and Times Square, perfect location!"

Reviewed on Nov 13, 2026

ROW NYC
Pod Times Square

Pod Times Square

3 out of 5
400 W 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Nov 22 to Nov 23
CA $141
CA $209 total
Nov 22 - Nov 23
includes taxes & fees
Pod Times Square
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $314 per night from Nov 22 to Nov 23
CA $314
CA $430 total
Nov 22 - Nov 23
includes taxes & fees
Hyatt Grand Central New York
See all 11,130 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular City Island attractions

City Island Nautical Museum

You can spend an afternoon browsing the exhibits at City Island Nautical Museum during your trip to Bronx. While you're here, you can savor the top-notch restaurants.
See properties

What to do in City Island

Edge Immersive Observation Deck Ticket

Edge Immersive Observation Deck Ticket

CA $61
per adult
94% of travellers recommend
Edge Immersive Observation Deck Ticket
NYC Pub Crawl & Rooftop Clubbing Experience

NYC Pub Crawl & Rooftop Clubbing Experience

CA $35
per adult
NYC Pub Crawl & Rooftop Clubbing Experience
Tyrannosaurs rex skeleton in the American Museum of Natural History in New York

American Museum of Natural History Tickets

CA $50
per adult
82% of travellers recommend
American Museum of Natural History Tickets
See all activities 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 $993. 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.