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A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Caribbean Ski Vacations

Book a Fishing Hotel + Flight or Car together to unlock savings

Top Ski vacation packages in Caribbean

Price found within the past 48 hours. Click for updated prices.
  • Outdoor pool, sun loungers
    Sep 23 - Sep 27

    RIG Colonial Experience + Flight

    Zona Colonial
    4 nights
    3.0 star property
    8.2/10 - Very Good (150 reviews)
    "Muy atenta la joven en el desayuno. No me gustó que, al llegar 3:40pm no tenían las habitaciones disponibles, y me alojaron en una que tienen una bomba de agua al lado de ese edificio que se dispara constantemente y así pasa la noche entera. Lo cual no dejó dormir. Para colmo el poco espacio que tienen (pasillos, escaleras, lobby), estuvieron unos jóvenes filmando una “miniserie” hasta la 1 de la madrugada. INACEPTABLE. No volveré ni de gratis."
    Reviewed July 19, 2026
    Roundtrip • San Juan (SJU) - Santo Domingo (SDQ)
    SJU - SDQ • Nonstop SDQ - SJU • Nonstop
    $379
    $359
    per traveler
    found 1 day ago
    RIG Colonial Experience
  • Exterior
    Oct 10 - Oct 15

    Airisha Villa Paradise + Flight

    Los Patos
    5 nights
    3.5 star property
    5.8/10 - (8 reviews)
    Roundtrip • New York (JFK) - Santo Domingo (SDQ)
    JFK - SDQ • Nonstop SDQ - JFK • Nonstop
    $746
    $727
    per traveler
    found 11 hours ago
    Airisha Villa Paradise

Discover the most popular places to visit in Caribbean

An old church with a tiled roof, stone walls, and two bell towers.

Altos de Chavon Village

A replica 16th-century Mediterranean village perched on a rocky outcrop above the River Chavón.

Top Ski Caribbean Hotels

Outdoor pool, sun loungers

RIG Colonial Experience

RIG Colonial Experience
3.0 star property
606 mi from Caribbean
8.2 out of 10, Very Good, (150 reviews)
"Muy atenta la joven en el desayuno. No me gustó que, al llegar 3:40pm no tenían las habitaciones disponibles, y me alojaron en una que tienen una bomba de agua al lado de ese edificio que se dispara constantemente y así pasa la noche entera. Lo cual no dejó dormir. Para colmo el poco espacio que tienen (pasillos, escaleras, lobby), estuvieron unos jóvenes filmando una “miniserie” hasta la 1 de la madrugada. INACEPTABLE. No volveré ni de gratis."
$51 nightly
The price is $65
Aug 8 - Aug 9
Total with taxes and fees
RIG Colonial Experience
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.
See all properties in Caribbean

Planning your Caribbean ski vacation

What are some things I should consider when booking a Caribbean 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 ski packages?

Right now, ski trips start at just $359. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Caribbean?

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

Sensational ski trips to Caribbean start from $359. 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?

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

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

What are some of the best things to do in the Caribbean for budget travelers?

The Caribbean is much more than a luxury getaway experience. If you want to plan one of the best Caribbean vacations for cheap, make the most of self-guided street food tours and sample local delicacies such as Barbados' cou-cou and flying fish and Antigua's bread pudding. For a very modest entry fee, hike through tropical forests and cloud-capped mountains in Jamaica's Blue and John Crow Mountains National Park. And of course, enjoy a bounty of free beaches and the always stunning spectacle of the sun going down over the horizon.