Ski Vacations in Fire Island 2026

Photo by Carole Polney

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Flight and Ski hotel deals in Fire Island

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

Library Hotel by Library Hotel Collection

Manhattan

CA $1,050

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (1,008 reviews)

Wonderful hotel just off Bryant Park. Walking distance to Broadway and Central Park. Rooms for very cozy and the staff was very friendly. Continental breakfast was good. We’ll stay here again… just double check size of bed when you book, it could be smaller than you think?

Reviewed on Aug 31, 2026

1 Hotel Brooklyn Bridge

CA $2,168

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,013 reviews)

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $1,485

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (3,936 reviews)

The breakfast was well below expectations. Unusual set up to go to lobby level then be ushered up to the fifth floor to eat in a busy, crowded cafeteria setting. Staff was ordering people around to line up properly. Food was cold (eggs, pancakes), stale (muffins)and overcooked (pancakes) Cream, butter, syrup in individual packets was not great. Coffee cups the size of shot glasses. The food on the lobby level was not really better. Heated up food that been sitting for a while. Location was great, room was fine, check in staff was great besides talking us into the breakfast "promotion"

Reviewed on Sep 2, 2026

Mandarin Oriental, New York

Manhattan

CA $2,042

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (663 reviews)

Ink 48 Hotel

Manhattan

CA $1,201

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

8.4/10 Very good! (1,772 reviews)

Surprisingly wonderful all around.

Reviewed on Sep 2, 2026

Don't see what you're looking for?

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5* Ski holidays in Fire Island

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

Mandarin Oriental, New York

Manhattan

CA $2,042

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (663 reviews)

1 Hotel Brooklyn Bridge

CA $2,168

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,013 reviews)

The Plaza, A Fairmont Hotel

Manhattan

CA $4,427

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,007 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fire Island

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3 Night Ski holidays in Fire Island

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

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,162

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (3,334 reviews)

5th & 55th Residence Club

Manhattan

CA $4,082

per person

Nov 14 - Nov 17

found 10 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New York (JFK)

8.4/10 Very good! (5 reviews)

1 Hotel Brooklyn Bridge

CA $2,168

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,013 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fire Island

View all trips

4 Night Ski holidays in Fire Island

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

Hotel Beacon

Manhattan

CA $1,798

per person

Oct 12 - Oct 16

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.4/10 Exceptional! (1,511 reviews)

1 Hotel Brooklyn Bridge

CA $2,426

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,013 reviews)

Hotel Riu Plaza New York Times Square

Manhattan

CA $2,020

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (3,334 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fire Island

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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 $1,050. 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 34 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 34. With Expedia Rewards, you can earn points towards your next booking.