A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Ski vacation packages in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
  • Jan 14 - Jan 17

    voco Sarasota by IHG + Flight

    Central Sarasota
    3 nights
    3.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $1,375
    CA $920
    per traveller
    found 3 hours ago
    voco Sarasota by IHG
  • Jan 13 - Jan 18

    CW Resort + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (311 reviews)
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Nonstop TPA - YYZ • Nonstop
    CA $1,702
    CA $1,101
    per traveller
    found 1 day ago
    CW Resort
  • Jan 13 - Jan 18

    Saddlebrook Resort + Flight

    Wesley Chapel South
    5 nights
    4.0 star property
    8.2/10 - Very good (200 reviews)
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Nonstop TPA - YYZ • Nonstop
    CA $2,197
    CA $1,462
    per traveller
    found 5 hours ago
    Saddlebrook Resort
  • Jan 13 - Jan 18

    ChartHouse Clearwater Beach Marina Hotel + Flight

    Clearwater Beach
    5 nights
    2.0 star property
    9.6/10 - Exceptional (1,576 reviews)
    "Such a beautiful get away place to come too. Please continue to keep it a great place to be."
    Reviewed November 12, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Nonstop TPA - YYZ • Nonstop
    CA $1,373
    CA $934
    per traveller
    found 1 day ago
    ChartHouse Clearwater Beach Marina Hotel
  • Jan 14 - Jan 17

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.4/10 - Exceptional (623 reviews)
    "What a treat for us Minnesotans!!! Special place to stay. Clean, comfy, and cozy! We stayed in the Violet Cottage. Staff allowed us to hang for a bit on the beach (plus parking for our rental) after check-out. There is even a shower available for this exact purpose, which is extra handy and appreciated. Thank you! We hope to be back some day!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $1,702
    CA $1,180
    per traveller
    found 3 hours ago
    Cedar Cove Resort and Cottages

Plan the ultimate ski vacation in Legacy Trail

What are some benefits when booking ski vacations in Legacy Trail?

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 Legacy Trail?

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 Legacy Trail, 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 Legacy Trail with some as cheap as CA $920. 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 Legacy Trail. 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 33 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 Legacy Trail.

Can I book all-inclusive ski vacations in Legacy Trail?

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 Legacy Trail 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 Legacy Trail'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 Legacy Trail?

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 Legacy Trail. 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 33. With Expedia Rewards, you can earn points towards your next booking.