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.
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was CA $1,474, price is now CA $949 per person
CA $949
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (275 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,145, price is now CA $2,116 per person
CA $2,116
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,446, price is now CA $1,427 per person
CA $1,427
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,722, price is now CA $1,010 per person
CA $1,010
per person
Jan 15 - Jan 18
found 2 days ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $4,036, price is now CA $2,534 per person
CA $2,534
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
We had a wonderful stay! The hotel was very clean, the staff was friendly and welcoming, and our spacious, beautiful room was ready before check in time. The complimentary breakfast offered a great variety of options. The location was perfect close to Times Square and within walking distance of restaurants, nightlife, and the Theater District. We truly enjoyed our stay and would definitely stay here again! Highly recommend!

Reviewed on Nov 14, 2026

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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 $243 per night from Nov 22 to Nov 23
CA $243
CA $349 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (3,191 reviews)
"The hotel was great, the staff was great. Rooms were smaller but we did not mind that as we were prepared for that from the other reviews. The only real issue we had were the long waits for the elevators in the morning. However, the staff were helpful and we really enjoyed our stay. I would go back ..."

Reviewed on Nov 15, 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 $129 per night from Nov 22 to Nov 23
CA $129
CA $195 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 $330 per night from Nov 22 to Nov 23
CA $330
CA $449 total
Nov 22 - Nov 23
includes taxes & fees
Hyatt Grand Central New York
See all 11,340 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.
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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 $949. 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.