A lighthouse, a red-roofed building, and a wooden structure near a coastal area.
Photo by Carole Polney
Open Photo by Carole Polney

Fire Island Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Ski vacation packages in Fire Island

Price found within the past 48 hours. Click for updated prices.
  • Dec 13 - Dec 16

    The Wall Street Inn + Flight

    Manhattan
    3 nights
    3.0 star property
    8.8/10 - Excellent (1,006 reviews)
    "Great deal, super nice staff, cute place… the carpet in the room had crumbs and the room smelt of Doritos 😂😂 not a big deal. I’ll be back."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,293
    CA $830
    per traveller
    found 1 day ago
    The Wall Street Inn
  • Jan 14 - Jan 17

    The St. Regis New York + Flight

    Manhattan
    3 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
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • 1 stop
    CA $4,016
    CA $2,154
    per traveller
    found 1 day ago
    The St. Regis New York
  • Dec 21 - Dec 26

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (4,156 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $3,653
    CA $2,130
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Jan 14 - Jan 17

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • 1 stop
    CA $2,119
    CA $1,260
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Dec 10 - Dec 13

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    3 nights
    4.0 star property
    9.4/10 - Exceptional (565 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $3,530
    CA $2,242
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel

Discover the most popular places to visit in Fire Island

Top Ski Fire Island Hotels

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.

Plan the ultimate ski vacation in Fire Island

What are some benefits when booking ski vacations in Fire Island?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Fire Island?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Fire Island, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Fire Island with some as cheap as CA $830. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Fire Island. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 35 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Fire Island.

Can I book all-inclusive ski vacations in Fire Island?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Fire Island in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Fire Island's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Fire Island?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Fire Island. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 35. With Expedia Rewards, you can earn points towards your next booking.