City Island All inclusive Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top All-inclusive holiday packages in City Island
- JW Marriott Essex House New York
30 Jan - 3 FebJW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,001 reviews)Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct EWR - DUB • 1 stop£1,517£1,007found 1 day agoper traveller - The St. Regis New York
20 Jan - 25 JanThe St. Regis New York + Flight
Manhattan5 nights5.0 star property9.2/10 - 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, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • 1 stop£3,590£1,975found 12 hours agoper traveller - Topping Rose House
11 Jan - 17 JanTopping Rose House + Flight
Bridgehampton6 nights4.5 star property9.0/10 - Wonderful (165 reviews)Return • London (LON) - New York (JFK)LHR - JFK • Direct JFK - LHR • Direct£10,940£6,511found 16 hours agoper traveller - Eurostars The Chemists’ Club Hotel
27 Dec - 1 JanEurostars The Chemists’ Club Hotel + Flight
Manhattan5 nights4.0 star property9.4/10 - Exceptional (568 reviews)Return • London (LHR) - New York (JFK)LHR - LGA • 1 stop LGA - LHR • 1 stop£2,804£1,816found 1 day agoper traveller - 1 Hotel Central Park
28 Dec - 1 Jan1 Hotel Central Park + Flight
Manhattan4 nights5.0 star property9.0/10 - Wonderful (1,008 reviews)"Lovely hotel and great location. Loved it. I rated it good because I arrived early and as expected my room wasn't yet ready. No problem. I left my bags and asked that they be taken up when the room was ready. I came back much later in the day (after check in time) and room wasn't yet ready and my bags of course weren't taken up. When I expressed some frustration, the situation was immediately resolved. But, I still don't get the delay. They tried to make it up to me by leaving a bottle of..."Reviewed November 9, 2026Return • Edinburgh (EDI) - New York (JFK)EDI - JFK • Direct JFK - EDI • 1 stop£3,006£2,053found 17 hours agoper traveller
What to do in City Island
SUMMIT One Vanderbilt Experience Tickets
Edge Immersive Observation Deck Ticket
New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent
All-inclusive City Island holidays: everything you need to know
Can I book City Island all-inclusive holidays with airfare and meals?
Use the all-inclusive filter to find amazing all-inclusive package holidays to City Island, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.
Why should I book a City Island adults-only all-inclusive holiday?
If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to City Island and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.
Can I book last minute all-inclusive holidays to City Island?
Last-minute breaks are a great way to find very cheap all-inclusive holidays to City Island. If you can be flexible with your holiday dates, browse our best City Island deals and use the all-inclusive filter to add everything that makes your hols perfect.
Can I book a cheap all-inclusive City Island trip?
There are some nifty little tricks to find pocket-friendly all-inclusive breaks in City Island. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at £1,007 – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.
What should I look for when booking a 5-star all-inclusive holiday to City Island?
All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.
What should I consider when booking a City Island all-inclusive family holiday?
If you’re holidaying with tots in tow, book an all-inclusive City Island package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.
How can I find the best deals on all-inclusive holidays to City Island in 2026/2027?
There are great all-inclusive deals galore in City Island. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.
Can I book an all-inclusive City Island package with free cancellation and/or flexible dates?
Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.
Why should I book an all-inclusive City Island package holiday with Expedia?
With a huge range of all-inclusive City Island trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.