City Island Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top City Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Benjamin Royal Sonesta New York

The Benjamin Royal Sonesta New York

4.5 out of 5
Manhattan
per person
Sep 17 - Sep 20
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (1,011 reviews)
Great room , a lot of good places to eat nearby

Reviewed on Aug. 5, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 23 - Oct 26
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on Aug. 6, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Great staff clean rooms soon. Guacamole was one of the best I had in a long time.

Reviewed on Aug. 7, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Great place to stay and very convenient location.

Reviewed on Aug. 7, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
I enjoyed my short stay at this hotel. It has a modern, boutique feel to it and the staff were friendly and helpful. Our double room was clean and the space was sufficient for 2 people. We did not receive the free bottle of wine that was supposed to come with VIP access.

Reviewed on Aug. 8, 2025

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City Island Hotel Deals

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from Aug 17 to Aug 18
CA $229
CA $323 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (4,124 reviews)
"Really enjoyed the location. Just a block away from Broadway and a block away from Radio City. Subway station on site. Lots of transportation options. Our room was on the 8th level. Two queen beds. Minimal space to access clothes from luggage. Bathroom was adequate. Our fridge had some mold in it ..."

Reviewed on Aug. 6, 2025

Sheraton New York Times Square Hotel
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street, at Grand Central Terminal, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $244 per night from Aug 10 to Aug 11
CA $244
CA $348 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (5,900 reviews)
"Overall the place was nice and it was comfortable. Being right on top of the subway made it super convenient as well. I did feel a couple of the staff could have been a bit nicer. Very sharp and annoyed I asked for help. Customer service just isn't what it used to be."

Reviewed on Aug. 6, 2025

Hyatt Grand Central New York
Hotel St. James

Hotel St. James

2.5 out of 5
109 W. 45TH ST., New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Aug 10 to Aug 11
CA $231
CA $270 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (6,201 reviews)
"A lovely old hotel in a fabulous location, the bed blankets contain stains!!…plus long black hair in the bathroom area…not very clean"

Reviewed on Aug. 7, 2025

Hotel St. James
See all 10,657 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
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Discover the most popular places to visit in City Island

Times Square

Times Square

New York’s infamous neon wonderland is hustle and bustle at its best, and an essential stop for all tourists.

Times Square
Central Park showing flowers, a park and a pond

Central Park

Offering blissful respite from Manhattan’s concrete jungle, this is the perfect spot to rest weary feet or enjoy a picnic.

Central Park
Ed Sullivan Theater showing a city and signage as well as a large group of people

Broadway

Visit the dazzling theater district of one of the world’s most exciting cities. Enjoy the shopping, dining and street entertainment as well.

Broadway

What to do in City Island

SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

CA $71
per adult
92% of travellers recommend
SUMMIT One Vanderbilt Experience Tickets
Statue of Liberty & Ellis Island Tour + Pedestal Access

Statue of Liberty & Ellis Island Tour: All Options

CA $86
per adult
94% of travellers recommend
Statue of Liberty & Ellis Island Tour: All Options
Edge NYC

NYC Edge Observation Deck at Hudson Yards Admission Ticket

CA $54
per adult
84% of travellers recommend
NYC Edge Observation Deck at Hudson Yards Admission Ticket
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 $1,418. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.