Grand Cayman Ski Vacations

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Top Ski vacation packages in Grand Cayman

Price found within the past 48 hours. Click for updated prices.
The Sunshine Hotel and Suites

The Sunshine Hotel and Suites

$970
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9/10 Wonderful! (1,005 reviews)
Clean room. Get bed. Bathroom was clean.

Reviewed on Oct 12, 2026

The Grove and The Grove Too

The Grove and The Grove Too

Save 100% on your flight
$1,269
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.6/10 Exceptional! (259 reviews)
The property was very nice and the staff were very friendly. The unit was clean and the finishes were very modern. There were a few things lacking within the room such as no full length mirror, no iron, no sponge to wash the dishes. Also, the listing made it seem like they had beach chairs and umbrellas set up on the beach for you, but that is not the case. The give you beach items which you have to carry over yourself and set up. So I am not sure what the resort fee is for and the resort fee that they charge is very expensive per day.

Reviewed on Oct 15, 2026

Point West Premier Rentals

Point West Premier Rentals

Northwest Point
Save 100% on your flight
$1,612
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (28 reviews)
Black Urchin

Black Urchin

Save 100% on your flight
$6,860
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (3 reviews)
Shangri-La Boutique Bed & Breakfast

Shangri-La Boutique Bed & Breakfast

Save 100% on your flight
$1,057
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (222 reviews)
I love everything

Reviewed on Sep 23, 2026

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5* Ski vacations in Grand Cayman

Price found within the past 48 hours. Click for updated prices.
The Grove and The Grove Too

The Grove and The Grove Too

Save 100% on your flight
$1,269
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.6/10 Exceptional! (259 reviews)
The property was very nice and the staff were very friendly. The unit was clean and the finishes were very modern. There were a few things lacking within the room such as no full length mirror, no iron, no sponge to wash the dishes. Also, the listing made it seem like they had beach chairs and umbrellas set up on the beach for you, but that is not the case. The give you beach items which you have to carry over yourself and set up. So I am not sure what the resort fee is for and the resort fee that they charge is very expensive per day.

Reviewed on Oct 15, 2026

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

Save 100% on your flight
$3,529
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.6/10 Exceptional! (1,004 reviews)
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight
$3,708
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (1,005 reviews)
Beautiful ocean views and large pool area. Great service.

Reviewed on Oct 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Grand Cayman
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3 Night Ski vacations in Grand Cayman

Price found within the past 48 hours. Click for updated prices.
Point West Premier Rentals

Point West Premier Rentals

Northwest Point
$1,019
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (28 reviews)
The Grove and The Grove Too

The Grove and The Grove Too

Save 100% on your flight
$1,269
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.6/10 Exceptional! (259 reviews)
The property was very nice and the staff were very friendly. The unit was clean and the finishes were very modern. There were a few things lacking within the room such as no full length mirror, no iron, no sponge to wash the dishes. Also, the listing made it seem like they had beach chairs and umbrellas set up on the beach for you, but that is not the case. The give you beach items which you have to carry over yourself and set up. So I am not sure what the resort fee is for and the resort fee that they charge is very expensive per day.

Reviewed on Oct 15, 2026

Black Urchin

Black Urchin

$4,377
per person
Nov 30 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
10/10 Exceptional! (3 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Grand Cayman
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4 Night Ski vacations in Grand Cayman

Price found within the past 48 hours. Click for updated prices.
Point West Premier Rentals

Point West Premier Rentals

Northwest Point
$1,240
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (28 reviews)
The Grove and The Grove Too

The Grove and The Grove Too

$2,340
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.6/10 Exceptional! (259 reviews)
The property was very nice and the staff were very friendly. The unit was clean and the finishes were very modern. There were a few things lacking within the room such as no full length mirror, no iron, no sponge to wash the dishes. Also, the listing made it seem like they had beach chairs and umbrellas set up on the beach for you, but that is not the case. The give you beach items which you have to carry over yourself and set up. So I am not sure what the resort fee is for and the resort fee that they charge is very expensive per day.

Reviewed on Oct 15, 2026

Black Urchin

Black Urchin

Save 100% on your flight
$6,860
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (3 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Grand Cayman
View all trips

Planning your Grand Cayman ski vacation

What are some things I should consider when booking a Grand Cayman 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 Grand Cayman 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 $970. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Grand Cayman?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Grand Cayman. 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 Grand Cayman cost?

Sensational ski trips to Grand Cayman start from $970. 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 Grand Cayman?

The best time to hit the slopes in Grand Cayman 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 Grand Cayman 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 Grand Cayman 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 Grand Cayman with Expedia?

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

Things to do

Stingray Sandbar, Snorkeling, and Starfish Point

Stingray Sandbar, Snorkeling, and Starfish Point

$56
per adult
100% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
Horseback Beach Riding in the Grand Cayman

Horseback Beach Riding in the Grand Cayman

$100
per adult
94% of travellers recommend
Horseback Beach Riding in the Grand Cayman
Cayman 3 in 1 Adventure Reef Snorkeling, Starfish and Stingrays

Grand Cayman Stingray City, Starfish Point & Reef Snorkeling

$109
per adult
100% of travellers recommend
Grand Cayman Stingray City, Starfish Point & Reef Snorkeling
See all activities in Grand Cayman

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.