South Shore Ski Vacations

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Photo by Dan Sherman
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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and Ski hotel deals in South Shore

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Kaua'i Resort Lihue

The Royal Sonesta Kaua'i Resort Lihue

CA $2,438
per person
Oct 24 - Oct 31
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.2/10 Wonderful! (1,287 reviews)
1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

CA $7,831
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.2/10 Wonderful! (371 reviews)
Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

Poipu
CA $5,968
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.6/10 Exceptional! (1,008 reviews)
Absolutely Phenomenal resort! I was there celebrating my 50th birthday and they went above and beyond making my trip special! I even saw dolphins from our hotel room with an epic view of the ocean. I could not have asked for a better gift! We used the adults only pool, ate a couple of meals at the small restaurant on site, walked to the beach (so close), rented snorkel gear. We didn’t get a chance to use the transportation they offered to go to local spots, because we had our own car, but loved that they had that. Free parking too, that was wonderful! Tori was very sweet, helpful with great communication. Making my stay just perfect. I didn’t get a chance to get a spa treatment but I’m sure that would have been heavenly too Very grateful and will highly recommend Koloa Landing Resort!

Reviewed on Aug 22, 2026

OUTRIGGER Kauaʻi Beach Resort & Spa

OUTRIGGER Kauaʻi Beach Resort & Spa

CA $2,924
per person
Oct 24 - Oct 31
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Lihue (LIH)
8.4/10 Very good! (1,145 reviews)
Ko'a Kea Resort on Po'ipu Beach

Ko'a Kea Resort on Po'ipu Beach

Poipu
CA $4,434
per person
Oct 24 - Oct 31
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Lihue (LIH)
9.4/10 Exceptional! (1,003 reviews)
To start the hotel still has 2 charges pending on my credit card, I understand a hold to make sure we didn’t mess the room up. We did not, but it’s still pending and there is a second charge for $332 that we have no idea what’s it’s from. I only ordered 1 drink to the room and that was it. Additionally there were ants in our room. I understand it’s Hawai’i but if you’re going to charge so much and have rooms cleaned everyday I’d figure they could get rid of ants. Also on our vacation the hurricane hit and we were stuck in the room for a day. The alarm kept going off and they came to check our smoke alarm twice when no one was smoking in the whole floor.

Reviewed on Aug 19, 2026

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5* Ski holidays in South Shore

Price found within the past 48 hours. Click for updated prices.
Timbers Kauai Ocean Club & Residences

Timbers Kauai Ocean Club & Residences

CA $4,509
per person
Nov 7 - Nov 11
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Lihue (LIH)
9.6/10 Exceptional! (35 reviews)
Choose other resorts. The amenities for this resort are not worth the money. There is only one restaurant and its not open all the time. The beach is 1/2 mile walk. The beach is not just for this property but for many others. Staff is very friendly, but not much they can do about the issues.

Reviewed on Jun 17, 2026

1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

CA $7,831
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lihue (LIH)
9.2/10 Wonderful! (371 reviews)
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3 Night Ski holidays in South Shore

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Kaua'i Resort Lihue

The Royal Sonesta Kaua'i Resort Lihue

CA $1,876
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Lihue (LIH)
9.2/10 Wonderful! (1,287 reviews)
1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

CA $3,781
per person
Nov 19 - Nov 22
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Lihue (LIH)
9.2/10 Wonderful! (371 reviews)
Grand Hyatt Kauai Resort and Spa

Grand Hyatt Kauai Resort and Spa

Poipu
CA $2,559
per person
Sep 23 - Sep 26
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Lihue (LIH)
9.4/10 Exceptional! (1,006 reviews)
Great gym, beautiful pools, helpful staff.

Reviewed on Aug 24, 2026

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4 Night Ski holidays in South Shore

Price found within the past 48 hours. Click for updated prices.
2417 at Lihue Oceanfront Resort

2417 at Lihue Oceanfront Resort

CA $1,215
per person
Oct 2 - Oct 6
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
7/10 Good! (65 reviews)
1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

CA $4,361
per person
Oct 2 - Oct 6
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lihue (LIH)
9.2/10 Wonderful! (371 reviews)
The Cliffs at Princeville by ResorTime

The Cliffs at Princeville by ResorTime

CA $1,895
per person
Nov 7 - Nov 11
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Lihue (LIH)
8.8/10 Excellent! (42 reviews)
Spacious, clean, good location in Princeville and Hanalei.

Reviewed on Aug 23, 2026

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Plan the ultimate ski vacation in South Shore

What are some benefits when booking ski vacations in South Shore?

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 South Shore?

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 South Shore, 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 South Shore with some as cheap as CA $1,215. 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 South Shore. 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 19 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 South Shore.

Can I book all-inclusive ski vacations in South Shore?

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 South Shore 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 South Shore'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 South Shore?

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 South Shore. 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 19. With Expedia Rewards, you can earn points towards your next booking.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.