Chrissi Island Ski Vacations

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Top Ski vacation packages in Chrissi Island

Price found within the past 48 hours. Click for updated prices.
  • Oct 5 - Oct 11

    Creta Blue Boutique Hotel + Flight

    Hersonissos
    5 nights
    4.0 star property
    9.4/10 - Exceptional (257 reviews)
    "Our third stay. Always welcoming, lovely staff. Very clean rooms and facilities. Excellent restaurant. Beautiful pool area. We will return again one day."
    Reviewed July 4, 2026
    Roundtrip Toronto (YTO) - Heraklion (HER)
    YYZ - HER1 stop HER - YYZ1 stop
    CA $2,658
    CA $1,904
    per traveller
    found 13 hours ago
    Creta Blue Boutique Hotel
  • Sept 1 - Sept 7

    Ventale Island Breeze Resort + Flight

    Apokoronas
    5 nights
    5.0 star property
    9.6/10 - Exceptional (35 reviews)
    "Our stay at Vertali was made truly special by the outstanding customer service. Every member of the team was warm, welcoming, and genuinely committed to making our vacation memorable. From the moment we arrived until the day we left, we felt cared for and appreciated. A very special thank you to Kiki, whose kindness, professionalism, and positive energy stood out every single day. She consistently went above and beyond and made us feel like valued guests rather than just another room..."
    Reviewed July 9, 2026
    Roundtrip Montreal (YMQ) - Chania (CHQ)
    YUL - CHQ2 stops CHQ - YUL2 stops
    CA $3,848
    CA $2,626
    per traveller
    found 1 day ago
    Ventale Island Breeze Resort
  • Oct 5 - Oct 11

    Paralos Kosta Alímia + Flight

    Hersonissos
    5 nights
    5.0 star property
    9.6/10 - Exceptional (49 reviews)
    "Great experience, very clean, amazing food. Only wish the pool remained open into the evening."
    Reviewed July 24, 2026
    Roundtrip Toronto (YTO) - Heraklion (HER)
    YYZ - HER1 stop HER - YYZ1 stop
    CA $3,243
    CA $2,297
    per traveller
    found 13 hours ago
    Paralos Kosta Alímia
  • Aug 27 - Sept 2

    Castello Boutique Suites by the sea - Adults Only + Flight

    Agios Nikolaos
    5 nights
    5.0 star property
    7.6/10 - Good (5 reviews)
    "Beautiful Hotel in a Great Location, But Some Details Let It Down We recently stayed at Castello Boutique Suites in Sissi, Crete to celebrate our anniversary, and overall, we had a very good holiday. The hotel made a wonderful gesture by upgrading us to a larger suite with a private side pool, which felt so special and really set the tone for our stay. The suite itself was stylish and comfortable, the breakfast was excellent every morning, and the staff were consistently warm, welcoming, and..."
    Reviewed August 23, 2025
    Roundtrip Toronto (YYZ) - Heraklion (HER)
    YYZ - HER1 stop HER - YYZ2 stops
    CA $3,347
    CA $2,386
    per traveller
    found 1 day ago
    Castello Boutique Suites by the sea - Adults Only
  • Aug 31 - Sept 4

    Castello Infinity Suites - Adults Only + Flight

    Malevizi
    3 nights
    5.0 star property
    9.4/10 - Exceptional (58 reviews)
    "This was one of the most disappointing hotel experiences I’ve had. The Hotels.com listing is misleading and materially inaccurate. Its advertised the hotel as being on a white sandy beach with an exclusive beach bar, complete with photos suggesting exactly that. In reality, there is no exclusive beach bar and the nearest beach is public, rocky and nothing like the images or description (it’s a vile beach). Had the listing been accurate, I would never have booked this hotel. The problems didn’t..."
    Reviewed June 30, 2026
    Roundtrip Toronto (YYZ) - Heraklion (HER)
    YYZ - HER1 stop HER - YYZ2 stops
    CA $3,177
    CA $2,313
    per traveller
    found 1 day ago
    Castello Infinity Suites - Adults Only

Plan the ultimate ski vacation in Chrissi Island

What are some benefits when booking ski vacations in Chrissi 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 Chrissi 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 Chrissi 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 Chrissi Island with some as cheap as CA $1,904. 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 Chrissi 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 28 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 Chrissi Island.

Can I book all-inclusive ski vacations in Chrissi 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 Chrissi 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 Chrissi 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 Chrissi 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 Chrissi 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 28. With Expedia Rewards, you can earn points towards your next booking.