Chalk Sound Drive Ski Vacations

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Top Ski vacation packages in Chalk Sound Drive

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

Zenza Boutique Hotel

Turtle Cove
Save 100% on your flight
$1,548
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.4/10 Exceptional! (907 reviews)
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$9,709
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

SulMare at Taylor Bay Luxury Villas

SulMare at Taylor Bay Luxury Villas

Save 100% on your flight
$5,195
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (5 reviews)
Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight
$15,015
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.8/10 Exceptional! (30 reviews)
This was the ultimate experience for private Caribbean luxury! Everything looks and feels as the pictures show, and better! The food was amazing, even though only one dinner location, they changed the menu every evening of our 6 night stay, so it was not a downside at all. Beaches on beach bungalow extremely gorgeous and private! Highly recommend for secluded paradise. Just pack accordingly, there are no paved roads, it is very dusty going to/from restaurant and clubhouse in golf cart. It was a cool feature to have our own golf cart to explore the island, and we did! The room has high end Sonos speaker, but we brought our waterproof speaker which we kept in the golf cart for our rides. Weather was 85 day and night, bring lightweight dresses or shorts for evening, no wraps needed. All dining was outdoors so don’t have to worry about being too cold in air conditioning. Truly paradise.

Reviewed on Oct 11, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
Save 100% on your flight
$12,800
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
No reviews
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5* Ski vacations in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$9,709
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight
$15,015
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.8/10 Exceptional! (30 reviews)
This was the ultimate experience for private Caribbean luxury! Everything looks and feels as the pictures show, and better! The food was amazing, even though only one dinner location, they changed the menu every evening of our 6 night stay, so it was not a downside at all. Beaches on beach bungalow extremely gorgeous and private! Highly recommend for secluded paradise. Just pack accordingly, there are no paved roads, it is very dusty going to/from restaurant and clubhouse in golf cart. It was a cool feature to have our own golf cart to explore the island, and we did! The room has high end Sonos speaker, but we brought our waterproof speaker which we kept in the golf cart for our rides. Weather was 85 day and night, bring lightweight dresses or shorts for evening, no wraps needed. All dining was outdoors so don’t have to worry about being too cold in air conditioning. Truly paradise.

Reviewed on Oct 11, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
Save 100% on your flight
$12,800
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Chalk Sound Drive
View all trips

3 Night Ski vacations in Chalk Sound Drive

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

Rooftop Villa Collection

Grace Bay
$3,889
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
No reviews
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$7,804
per person
Nov 26 - Nov 29
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight
$4,043
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Providenciales (PLS)
9.8/10 Exceptional! (30 reviews)
This was the ultimate experience for private Caribbean luxury! Everything looks and feels as the pictures show, and better! The food was amazing, even though only one dinner location, they changed the menu every evening of our 6 night stay, so it was not a downside at all. Beaches on beach bungalow extremely gorgeous and private! Highly recommend for secluded paradise. Just pack accordingly, there are no paved roads, it is very dusty going to/from restaurant and clubhouse in golf cart. It was a cool feature to have our own golf cart to explore the island, and we did! The room has high end Sonos speaker, but we brought our waterproof speaker which we kept in the golf cart for our rides. Weather was 85 day and night, bring lightweight dresses or shorts for evening, no wraps needed. All dining was outdoors so don’t have to worry about being too cold in air conditioning. Truly paradise.

Reviewed on Oct 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chalk Sound Drive
View all trips

4 Night Ski vacations in Chalk Sound Drive

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

Dream Villas Provo

Blue Hills
$1,653
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.4/10 Exceptional! (82 reviews)
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$10,475
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
$5,047
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Chalk Sound Drive
View all trips

Planning your Chalk Sound Drive ski vacation

What are some things I should consider when booking a Chalk Sound Drive ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Chalk Sound Drive ski packages?

Right now, ski trips start at just $1,548. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Chalk Sound Drive?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Chalk Sound Drive. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Chalk Sound Drive cost?

Sensational ski trips to Chalk Sound Drive start from $1,548. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Chalk Sound Drive?

The best time to hit the slopes in Chalk Sound Drive depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Chalk Sound Drive ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Chalk Sound Drive ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Chalk Sound Drive with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Chalk Sound Drive ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

More vacations you might like

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