Chalk Sound Drive Ski Vacations

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Flight and Ski hotel deals in Chalk Sound Drive

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

Windsong on the Reef

Grace Bay

CA $3,217

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.2/10 Wonderful! (1,207 reviews)

Rooftop Villa Collection

Grace Bay

CA $4,569

per person

Oct 15 - Oct 19

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Providenciales (PLS)

No reviews

Bungalows at Windsong on the Reef

Grace Bay

CA $3,677

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9/10 Wonderful! (100 reviews)

We had an AMAZING stay. The property is well maintained. Amenities convenient. Food GOOD. Staff EXCEPTIONAL! Shout Out to Raheem!

Reviewed on Aug 6, 2026

The Strand Turks and Caicos

Cooper Jack Bay Settlement

CA $4,891

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.8/10 Exceptional! (31 reviews)

The Shore Club Turks and Caicos

Long Bay Hills

CA $4,657

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.4/10 Exceptional! (965 reviews)

Excellent. Beautiful, staff was amazing

Reviewed on Aug 12, 2026

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5* Ski holidays in Chalk Sound Drive

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

Beachfront at Windsong on the Reef

Grace Bay

CA $4,454

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.2/10 Wonderful! (176 reviews)

I’d recommend

Reviewed on Aug 12, 2026

The Strand Turks and Caicos

Cooper Jack Bay Settlement

CA $4,891

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.8/10 Exceptional! (31 reviews)

The Shore Club Turks and Caicos

Long Bay Hills

CA $4,657

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Providenciales (PLS)

9.4/10 Exceptional! (965 reviews)

Excellent. Beautiful, staff was amazing

Reviewed on Aug 12, 2026

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See all available trips from Columbus to Chalk Sound Drive

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3 Night Ski holidays in Chalk Sound Drive

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

Windsong on the Reef

Grace Bay

CA $1,700

per person

Sep 28 - Oct 1

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Providenciales (PLS)

9.2/10 Wonderful! (1,207 reviews)

Rooftop Villa Collection

Grace Bay

CA $2,665

per person

Oct 25 - Oct 28

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Providenciales (PLS)

No reviews

Long Bay Beach Club

Long Bay Hills

CA $3,471

per person

Oct 25 - Oct 28

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Providenciales (PLS)

10/10 Exceptional! (4 reviews)

Reviewed on Aug 3, 2026

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4 Night Ski holidays in Chalk Sound Drive

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

Dream Villas Provo

Blue Hills

CA $2,342

per person

Sep 20 - Sep 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

9.2/10 Wonderful! (76 reviews)

I would recommend this place for a relaxing getaway; it’s not really suited for those who prefer an active vacation. The house itself is great—good soundproofing and plenty of air conditioning units that handle the heat well. It was generally well-equipped. It was clean, with no insects or unpleasant odors. The rooftop pool was always cooler than the ocean, which was very refreshing in the heat. Parking was along the road; we had no issues with our car over the course of the week. The water was very warm in August—no need to acclimate to the temperature at all. Communication with the owners was smooth and easy. There were sometimes stray dogs outside, but they were calm and friendly; they didn't try to enter the house or bark. Driving on the island is very easy, even though everyone drives at twice the speed limit; I only saw the police a couple of times.One thing I didn't love—though this is more about the trip in general than the house—was the weather: it was hotter than usual (30°C / 86°F) with high humidity, so it was best to spend the hours between 11:00 AM and 4:00 PM resting indoors or having lunch. The best times to be outside were 7:00–10:00 AM and 4:00–7:00 PM. The sun loungers on the roof aren't the newest and are dusty, but if you use beach towels, there’s no problem. There were rains, but they were very brief and light. There was quite a bit of broken glass on the beach; over the course of the week, we collected and removed the shards ourselves.

Reviewed on Aug 14, 2026

Rooftop Villa Collection

Grace Bay

CA $3,942

per person

Sep 20 - Sep 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

No reviews

Long Bay Beach Club

Long Bay Hills

CA $8,858

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Providenciales (PLS)

10/10 Exceptional! (4 reviews)

Reviewed on Aug 3, 2026

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What are some benefits when booking ski vacations in Chalk Sound Drive?

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 Chalk Sound Drive?

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 Chalk Sound Drive, 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 Chalk Sound Drive with some as cheap as CA $1,700. 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 Chalk Sound Drive. 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 42 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 Chalk Sound Drive.

Can I book all-inclusive ski vacations in Chalk Sound Drive?

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 Chalk Sound Drive 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 Chalk Sound Drive'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 Chalk Sound Drive?

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 Chalk Sound Drive. 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 42. With Expedia Rewards, you can earn points towards your next booking.