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
$1,391
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.4/10 Exceptional! (907 reviews)
Le Vele Resort

Le Vele Resort

Grace Bay
$2,089
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (69 reviews)
Clean room. Beautiful beach. Beautiful beach view from balcony. Very friendly staff

Reviewed on Oct 23, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$15,645
per person
Jan 4 - Jan 10
found 1 day ago
Roundtrip non-stop 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

$12,994
per person
Jan 9 - Jan 15
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

South Bank

South Bank

Long Bay Hills
$2,641
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (19 reviews)
Amazing 👏

Reviewed on Oct 18, 2026

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5* Ski vacations in Chalk Sound Drive

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

South Bank

Long Bay Hills
$2,641
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (19 reviews)
Amazing 👏

Reviewed on Oct 18, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$15,645
per person
Jan 4 - Jan 10
found 1 day ago
Roundtrip non-stop 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

$12,994
per person
Jan 9 - Jan 15
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

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3 Night Ski vacations in Chalk Sound Drive

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

Le Vele Resort

Grace Bay
$1,468
per person
Jan 3 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Providenciales (PLS)
9.2/10 Wonderful! (69 reviews)
Clean room. Beautiful beach. Beautiful beach view from balcony. Very friendly staff

Reviewed on Oct 23, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$6,222
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

The Shore Club Turks and Caicos

The Shore Club Turks and Caicos

Long Bay Hills
Save 100% on your flight
$1,755
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.4/10 Exceptional! (986 reviews)
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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
$1,652
per person
Jan 4 - Jan 8
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
$11,462
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Le Vele Resort

Le Vele Resort

Grace Bay
$2,111
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (69 reviews)
Clean room. Beautiful beach. Beautiful beach view from balcony. Very friendly staff

Reviewed on Oct 23, 2026

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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?

Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $1,391. 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 $1,391. 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.