City Island Vacation Packages

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Top City Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wayne Inn

The Wayne Inn

2 out of 5
Price was CA $1,652, price is now CA $913 per person
CA $913
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
6.8/10 (289 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,645, price is now CA $1,935 per person
CA $1,935
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (666 reviews)
Customer Service is outstanding

Reviewed on Apr 23, 2026

The William Vale

The William Vale

5 out of 5
Price was CA $2,813, price is now CA $1,705 per person
CA $1,705
per person
Jul 19 - Jul 24
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,050 reviews)
Loved the room! I found myself just looking out the window and on the balcony. With the right weather, I would have never left. It is a great spot and I’d love to go back!

Reviewed on May 1, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,979, price is now CA $1,239 per person
CA $1,239
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,468 reviews)
Very clean hotel. A bit noisy from the corridor or next room. Otherwise perfect.

Reviewed on May 6, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,948, price is now CA $1,220 per person
CA $1,220
per person
Jul 19 - Jul 24
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
So this is a basic hotel in an expensive town. It wants to be special, but it isn’t. It is honestly a little weird. Here’s my story: Check in: mildly annoyed desk agent would not check me in, spouse name on reservation. Ugh. I booked Expedia so I didn’t think to add myself. So, we are at an impass. But no! There’s an answer! Just call here on your cell, and have her tell us it is ok for you to check in and add yourself to the reservation. Done. Fine. What was the point of that stupid exercise? But, I have permission. Great. Agent then makes a weird production of taking out latex gloves, snapping them on, TO TOUCH MY ID. Ok . Whatever. Hotel is like 1/2 a city block square. I ask: how do I get to my room? Reasonable question. I ask because I see on the way in there is parking all around the hotel. “It’s up the stairs or elevator to floor 2. Follow the signs.” As I walk 5 minutes, I realize I should have driven to the back of the hotel. One of the most bizarre passive aggressive check ins I’ve ever had. Shampoo is a soap bar. Weird Have to ask for hair conditioner (wife’s issue) Weird Breakfast was Ok, but not special. Breakfast area espresso machine was nice. I suspect this is a local event venue, and I’m not local. So Won’t return.

Reviewed on May 6, 2026

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City Island Hotel Deals

Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
228 W 47th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 10 to May 11
CA $173
CA $266 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (5,504 reviews)
Very safe, convenient location in the theatre district. Stay here every time I visit the city.

Reviewed on May 5, 2026

Hotel Edison Times Square
NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
481 Eighth Ave. New York NY
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from May 10 to May 11
CA $203
CA $300 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (6,706 reviews)
Everything was good

Reviewed on May 6, 2026

NEW YORKER BY LOTTE HOTELS
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 $298 per night from May 10 to May 11
CA $298
CA $401 total
May 10 - May 11
includes taxes & fees
7.4/10 Good! (7,836 reviews)
Yes

Reviewed on May 6, 2026

Sheraton New York Times Square Hotel
See all 12,224 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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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

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
Grand Central Terminal

Grand Central Terminal

This majestic, lively hub for commuters is a must-see for architecture buffs.

Grand Central Terminal

What to do in City Island

SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

CA $66
per adult
94% of travellers recommend
SUMMIT One Vanderbilt Experience Tickets
Madame Tussauds New York Celebrity Wax Museum

Madame Tussauds New York Celebrity Wax Museum

CA $39
per traveller
90% of travellers recommend
Madame Tussauds New York Celebrity Wax Museum
Top of the Rock Observation Deck

Top of the Rock Observation Deck

CA $71
per adult
90% of travellers recommend
Top of the Rock Observation Deck
See all activities in City Island

Frequently asked questions

Can I cancel my flight booking to City Island due to COVID-19?
If you haven't booked yet, read the terms and conditions of your preferred airline. If you've already reserved your flight to City Island, head to our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to City Island that have flexible change policies?
Search for your affordable airfares to City Island, then mark the "No change fee" box directly under the "Flexible change policies" heading. It's that simple. We know that plans change and flexibility matters, so book with confidence with Expedia.
What are some of the general tips for travelers to City Island during the COVID-19 outbreak?
With new restrictions and safety precautions to follow, travel looks a little different at present. Here's what you should know before you pack your bags for City Island:
  • Research if any travel restrictions apply to your origin and destination before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as undergoing health assessments.
  • Wear a face mask even during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • To reduce the risk of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • TSA now allows passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will need to be removed from your bag for X-ray screening.
  • To reduce handling during screening, put items such as your phone, keys and wallet into your carry-on rather than into the bins.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA employee will need to open your bag for inspection.

Which airlines fly to City Island?
Delta runs flights into or near City Island, including 4895 that travel to John F. Kennedy Intl. Airport (JFK) each month. Choose your travel dates and then secure your fare early to bag a bargain.
How can I find cheap tickets to City Island?
Book well ahead, consider nearby airports, use miles or points — there are loads of ways! One more is to use Expedia's "flexible dates" function. Find your City Island flight, then compare the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to City Island was .
How much is a flight to City Island?
In the last seven days, return tickets to City Island sold for as little as and reached a maximum of . For one-way trips taking off from (), the lowest price during this time was just .
What are the most popular airports to fly into in City Island?
City Island's main entryway is John F. Kennedy Intl. Airport (JFK). Get your next exciting journey underway by securing a seat on one of the 13452 monthly flights to this destination.
When is the cheapest time to fly to City Island?
If you'd rather spend your vacation cash enjoying the delights of City Island rather than on your journey there, depart early in the week. The cheapest day to travel is generally Tuesday, with Monday coming in second. With many people keeping their travel to weekends, Saturday tends to have the costliest airfares.
How much is a plane ticket to City Island?
Airfares ranged anywhere from to over the last seven days. When you're ready to book, we'll be ready to help you find an awesome deal to City Island.
Which airlines with flights to City Island employ COVID-19 cleanliness policies?
In an effort to reduce contact between passengers and flight attendants during the current pandemic, airlines have taken social distancing and other protective measures to the skies. Just some of these are:
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.