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

City Island Ski Holidays

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Top Ski holiday packages in City Island

Price found within the past 48 hours. Click for updated prices.
  • 28 Dec - 2 Jan

    The William Hotel Midtown, New York + Flight

    Manhattan
    5 nights
    3.5 star property
    9.4/10 - Exceptional (304 reviews)
    Return • Sydney (SYD) - New York (JFK)
    SYD - JFK • 1 stop JFK - SYD • 1 stop
    AU$6,911
    AU$5,155
    per traveller
    found 1 day ago
    The William Hotel Midtown, New York
  • 17 Dec - 23 Dec

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.2/10 - Wonderful (4,184 reviews)
    "The whole elevator experience is dreadful! If you are trying to access the elevator during peak times expect 20min plus wait times. This becomes very annoying when the only lobby bathroom and gym is in the cellar and you have to wait a long time to go up or down one flight. The hotel refused to let us use the stairs even to go down just the one flight of stairs. The happy hour menu looked good, however the drinks were horrible. Only part took in it once. $24.00 for breakfast is outrageous. Spend..."
    Reviewed November 12, 2026
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$8,355
    AU$6,085
    per traveller
    found 12 hours ago
    Hotel Riu Plaza Manhattan Times Square
  • 17 Dec - 23 Dec

    The St. Regis New York + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - 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, 2026
    Return • Sydney (SYD) - New York (JFK)
    SYD - JFK • 1 stop JFK - SYD • 1 stop
    AU$23,207
    AU$17,016
    per traveller
    found 1 day ago
    The St. Regis New York
  • 17 Dec - 23 Dec

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (3,455 reviews)
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$7,845
    AU$5,807
    per traveller
    found 12 hours ago
    Hotel Riu Plaza New York Times Square
  • 28 Dec - 2 Jan

    Hotel Beacon + Flight

    Manhattan
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,563 reviews)
    "Staff was so helpful and friendly to us and our kids!"
    Reviewed November 11, 2026
    Return • Sydney (SYD) - New York (JFK)
    SYD - JFK • 1 stop JFK - SYD • 1 stop
    AU$7,094
    AU$5,512
    per traveller
    found 1 day ago
    Hotel Beacon

Discover the most popular places to visit in City Island

What to do in City Island

How to find City Island ski packages?

What kind of ski holiday packages are available in City Island?

Expedia offers a wide variety of ski holiday packages. To find out what packages are currently available, just search Expedia for City Island ski packages 2026 and start planning your next ski trip.

How can I book a ski holiday in City Island with Expedia?

Go to the search bar and select “Packages”. Then, choose your destination and the dates of your stay, and browse the list of City Island ski packages to find your perfect ski holiday.

Are ski holidays in City Island suitable for families?

City Island ski holidays can be a great option for families. You can enrol your children in skiing lessons if they’re beginners or spend the days on the slopes with them if they’re already experienced skiers. If your children are too young to ski themselves, look for family-friendly accommodation that offers childcare services and activities for non-skiing family members.

What’s the best way to plan a skiing holiday in in City Island?

Planning a ski holiday to City Island couldn’t be simpler. Just choose your destination and when you want to go, and Expedia will take care of the rest. Once you’ve selected where and when you want to go, Expedia will provide you with several ski packages for that time and place for you to choose from.

What are some tips for choosing a ski package in in City Island?

Before searching for ski packages to City Island, define your priorities. Are you looking for a family-friendly resort, luxury accommodations, budget-friendly options, or specific ski terrain? Knowing your preferences will help you narrow down your choices.

How can I find excellent deals on ski holidays in in City Island?

One of the most reliable ways to get a good deal for 2026 is to book your City Island ski holiday well in advance. Resorts often offer early booking discounts, and you’ll have a wider selection of accommodations to choose from.

How can I grab last-minute ski holiday deals in City Island?

Just enter your dates and see what’s available. This way you might be able to nab some great last-minute City Island ski packages.

Are pet-friendly ski holiday packages available in City Island?

To find pet-friendly City Island ski packages in 2026, once you’ve entered your dates, use the filters on the left and select “Pet-friendly” under “Amenities” and the pet-friendly ski resort packages will show up.

How can I find great weekend ski holiday packages in City Island?

Enter your weekend dates and search Expedia’s City Island ski trip packages to find the ones that are available for the weekend of your choice. You can sort by price to find City Island ski holidays that suit your wallet.

How can I find the cheapest ski holidays in in City Island?

Once you’ve entered your travel dates, use the sort by filter at the top right to sort by price and find City Island ski holidays that won’t break the bank. Plus, booking well in advance can help you find cheaper rates. Be sure to check out Expedia’s City Island ski packages including flights as you could save money by booking everything together.

Why should I book a ski holiday package in City Island with Expedia?

Expedia lets you bundle up your stay, flight, and car rental for some cool discounts on City Island ski packages that will have you carving through the powder without burning a hole in your pocket.

Can I cancel my ski holiday booking in City Island with Expedia?

Yes, numerous City Island ski packages offer free cancellation, giving you the freedom to put the brakes on your trip in the event of unforeseen circumstances.