A river winding through a densely populated residential area with numerous houses and docks along the water.

City Island Beach Vacations

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Top Beach vacation packages in City Island

Price found within the past 48 hours. Click for updated prices.
  • Jan 16 - Jan 22

    Holiday Inn Express New York City Times Square by IHG + Flight

    Manhattan
    6 nights
    3.0 star property
    7.6/10 - Good (3,318 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $1,017
    $589
    per traveler
    found 2 days ago
    Holiday Inn Express New York City Times Square by IHG
  • Jan 16 - Jan 22

    INNSiDE by Meliá New York Nomad + Flight

    Manhattan
    6 nights
    4.5 star property
    9.2/10 - Wonderful (2,374 reviews)
    "Had a great time"
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    $1,229
    $645
    per traveler
    found 2 days ago
    INNSiDE by Meliá New York Nomad
  • Jan 20 - Jan 24

    JW Marriott Essex House New York + Flight

    Manhattan
    4 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $1,529
    $851
    per traveler
    found 2 days ago
    JW Marriott Essex House New York
  • Jan 16 - Jan 22

    The Langham, New York, Fifth Avenue + Flight

    Manhattan
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $3,574
    $2,020
    per traveler
    found 2 days ago
    The Langham, New York, Fifth Avenue
  • Jan 16 - Jan 22

    Loews Regency New York Hotel + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $3,064
    $1,786
    per traveler
    found 2 days ago
    Loews Regency New York Hotel

Discover the most popular places to visit in City Island

What to do in City Island

Find your perfect City Island beach vacation

How do I book the best City Island beach vacation packages?

Life’s a beach when you dive into our brilliant City Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in City Island?

A rental steps from the shore creates an amazingly affordable City Island beach vacation. Seaside sojourns during low season start from $589. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in City Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a City Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a City Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find City Island beach vacation deals?

Sort your search results by deals to delight in amazing City Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a City Island beach trip with free cancellation and/or flexible dates?

Just like the City Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my City Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in City Island. (OK, maybe not that last part.)