Caribbean Islands Ski Vacations 2026

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Top Ski vacation packages in Caribbean Islands

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

El Conquistador Resort

Cabezas

$447

per person

Sep 9 - Sep 11

found 5 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9/10 Wonderful! (3,551 reviews)

Take your own WiFi property WiFi is poor and does not work from time to time.

Reviewed on Aug 10, 2026

Bahia Principe Explore Legend - Hyatt Inclusive Collection - All Inclusive

Bávaro

$961

per person

Oct 10 - Oct 13

found 10 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Punta Cana (PUJ)

8.4/10 Very Good! (2,446 reviews)

First time to DR and to an all inclusive hotel. Bahia Principe Legend was absolutely amazing! Our daughter, and us, enjoyed every second. The people were friendly, helpful and kind. Christina, our family concierge, was just wonderful. Excursions were amazing (monkey land highly recommend). Buffet food was okay, it was buffet food. The dinners were amazing and so were the servers, all went above and beyond to make sure our stay was special. Truly a memorable time that will forever be in our hearts. Will truly visit again!

Reviewed on Aug 10, 2026

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

$1,340

per person

Sep 9 - Sep 12

found 8 hours ago

Roundtrip flight included

New York (NYC) to Vieux Fort (UVF)

8.6/10 Excellent! (205 reviews)

Grand Bavaro Princess - All Inclusive

Bávaro

$734

per person

Sep 9 - Sep 12

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Punta Cana (PUJ)

8.2/10 Very Good! (4,152 reviews)

Couples Swept Away All Inclusive

$1,164

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to Montego Bay (MBJ)

9/10 Wonderful! (1,012 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

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5* Ski vacations in Caribbean Islands

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

Grand Bavaro Princess - All Inclusive

Bávaro

$734

per person

Sep 9 - Sep 12

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Punta Cana (PUJ)

8.2/10 Very Good! (4,152 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

View all trips

3 Night Ski vacations in Caribbean Islands

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

El Conquistador Resort

Cabezas

$705

per person

Sep 9 - Sep 12

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to San Juan (SJU)

9/10 Wonderful! (3,551 reviews)

Take your own WiFi property WiFi is poor and does not work from time to time.

Reviewed on Aug 10, 2026

Bahia Principe Explore Legend - Hyatt Inclusive Collection - All Inclusive

Bávaro

$961

per person

Oct 10 - Oct 13

found 10 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Punta Cana (PUJ)

8.4/10 Very Good! (2,446 reviews)

Reviewed on Aug 10, 2026

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

$1,340

per person

Sep 9 - Sep 12

found 8 hours ago

Roundtrip flight included

New York (NYC) to Vieux Fort (UVF)

8.6/10 Excellent! (205 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

View all trips

4 Night Ski vacations in Caribbean Islands

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

Grand Bavaro Princess - All Inclusive

Bávaro

$880

per person

Sep 9 - Sep 13

found 9 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Punta Cana (PUJ)

8.2/10 Very Good! (4,152 reviews)

Bahia Principe Explore Legend - Hyatt Inclusive Collection - All Inclusive

Bávaro

$957

per person

Oct 10 - Oct 14

found 15 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Punta Cana (PUJ)

8.4/10 Very Good! (2,446 reviews)

Reviewed on Aug 10, 2026

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

$1,996

per person

Oct 10 - Oct 14

found 12 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Vieux Fort (UVF)

8.6/10 Excellent! (205 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

View all trips

What are some things I should consider when booking a Caribbean Islands 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 Caribbean Islands 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 $447. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Caribbean Islands?

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

Sensational ski trips to Caribbean Islands start from $447. 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 Caribbean Islands?

The best time to hit the slopes in Caribbean Islands 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 Caribbean Islands 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 Caribbean Islands 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 Caribbean Islands with Expedia?

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

Top Ski Caribbean Islands Hotels

2 - Exotic Bungalow T2 & Large Garden near beach

LA TRINITE MARTINIQUE

9 hours drive from Oyster Bay Marina

Stay at this vacation home in La Trinité. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Plage des Raisiniers and Plage de l'Autre Bord ...

9.4/10 Exceptional! (16 reviews)

Beautiful Garden, convenience, comfortable, economical, perfect.

"We were very pleased with the bungalow. We stayed 3 nights, 2/2/17 - 2/5/17, and would stay longer if we had more vacation time. We liked the outside but under cover dinning area. The kitchen was well stocked with all essentials. The climate controlled bedroom was adequate in size although we would ..."

Reviewed on Feb 13, 2017

Bay Gardens Hotel

Rodney Bay Village Gros Islet

11 hours drive from Oyster Bay Marina

Book a stay at this beach hotel in Gros Islet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...

8/10 Very Good! (1,008 reviews)

"The reception was the only quality about the property I will give a 5 star. The room was average. Not bad, but nothing to write home about. The food experience was definitely sub par. It was repetitive, bland, and samey. How could fried plantains not be tasty? Most disappointing were the non responses. ..."

Reviewed on Aug 8, 2026

Grand Bavaro Princess - All Inclusive

Playas De Bavaro Punta Cana La Altagracia

13 hours drive from Oyster Bay Marina

Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...

See all 86,548 properties in Caribbean Islands

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.