Oak Island Ski Vacations

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Flight and Ski hotel deals in Oak Island

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

Westgate Flamingo Bay Resort

Spring Valley

CA $885

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Las Vegas (LAS)

8.8/10 Excellent! (1,003 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,187

per person

Oct 18 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite- NO RESORT FEE

CA $1,835

per person

Oct 22 - Oct 26

found 2 days ago

Roundtrip flight included

Toronto (YTO) to Las Vegas (LAS)

8.6/10 Excellent! (4 reviews)

The view was gorgeous at night with all the lights. We loved it! ~ Always Grateful. ~

Reviewed on May 7, 2026

Pelican Hotel

South Beach

CA $1,241

per person

Oct 18 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

9.2/10 Wonderful! (492 reviews)

I don’t recommend this place to anyone Bad service Aggressive staff No smiles Party place Food not the best Pass on this one … the reception employee night shifts will not even get up to help Or will call the cops if his not in control I would not go there so many nicer places in Miami Beach

Reviewed on Aug 12, 2026

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5* Ski holidays in Oak Island

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

Red Rock Casino, Resort and Spa

Summerlin South

CA $870

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Las Vegas (LAS)

9.2/10 Wonderful! (2,788 reviews)

The hotel, casino, and restaurants were excellent. Hotel cleaning staff were especially good and pleasant. With the movie theater, pool, and bowling alley at the property and the shopping area right next to it, there is plenty to do. The staff at the check-in desk told us all king rooms were booked, but 10 minutes later another couple on our reservation checked in and were offered their choice of king or queen guest rooms.

Reviewed on Aug 14, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,187

per person

Oct 18 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

EAST Miami Residences

Brickell

CA $3,010

per person

Oct 18 - Oct 25

found 22 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

9.2/10 Wonderful! (143 reviews)

Prime location. Connected to shopping mall and high level restaurants. Within walking distance of other restaurants and speakeasies that make Brickell special and busy. Love the amenities in the hotel (pool and fitness center and restaurant on site were great). Great hotel

Reviewed on Aug 9, 2026

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3 Night Ski holidays in Oak Island

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

Radio Hotel

Manhattan

CA $927

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,493 reviews)

Ass community, a decent hotel tho

Reviewed on Aug 14, 2026

The Rose Premium Suite at MGM Signature

CA $1,005

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Las Vegas (LAS)

5/10 (6 reviews)

I felt like the walk from the front entrance was quite the distance and you could only catch ride shares from the front entrance. Discovered this the hard way. This particular room had to be close to the pool and club area as you could hear the music late at night.

Reviewed on Jun 15, 2026

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4 Night Ski holidays in Oak Island

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

Harrah’s Las Vegas – A Caesars Rewards Destination

Las Vegas Strip

CA $899

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Las Vegas (LAS)

8/10 Very good! (16,155 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $12,239

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

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What are some benefits when booking ski vacations in Oak 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 Oak 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 Oak 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 Oak Island with some as cheap as CA $870. 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 Oak 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 44 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 Oak Island.

Can I book all-inclusive ski vacations in Oak 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 Oak 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 Oak 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 Oak 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 Oak 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 44. With Expedia Rewards, you can earn points towards your next booking.