An aerial view of a tropical island with clear turquoise waters and a sandy beach.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Roosevelt Roads Ski Vacations

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Top Ski vacation packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Feb 3

    Hotel Puerto Valdes + Flight

    Puerta de Tierra
    5 nights
    4.0 star property
    8.8/10 - Excellent (766 reviews)
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    Save 100% on your flight
    CA $2,962
    CA $1,751
    per traveller
    found 1 day ago
    Hotel Puerto Valdes
  • Jan 20 - Jan 26

    Castillo Caribe by Otium + Flight

    Condado
    6 nights
    2.0 star property
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $4,525
    CA $2,818
    per traveller
    found 16 hours ago
    Castillo Caribe by Otium
  • Jan 11 - Jan 17

    Hyatt Regency Grand Reserve Puerto Rico + Flight

    Zarzal
    6 nights
    4.0 star property
    9.2/10 - Wonderful (3,536 reviews)
    "Excellent resort with helpful and friendly staff. The big pool and views of the beach were our favorite part of the resort. The bartenders made great drinks and gave good advice on places to try and explore. We can’t wait to go back again."
    Reviewed November 11, 2026
    Roundtrip • Hamilton (YHM) - San Juan (SJU)
    YHM - SJU • 1 stop SJU - YHM • 2 stops
    Save 100% on your flight
    CA $3,933
    CA $2,515
    per traveller
    found 17 hours ago
    Hyatt Regency Grand Reserve Puerto Rico
  • Jan 20 - Jan 26

    Casa Elena by Otium + Flight

    Santurce
    6 nights
    3.0 star property
    8.6/10 - Excellent (39 reviews)
    "The biggest problem is that the windows do not have glass panes; they only have screens. As a result, whenever the blinds are opened, all the heat and humidity from outside enter the apartment. This makes it difficult to keep the apartment comfortable and well ventilated. In practice, the apartment has to remain dark because opening the blinds to let in natural light also allows a significant amount of heat and humidity to enter. The appartment is confortable, clean, well located and with easy..."
    Reviewed September 12, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $3,060
    CA $2,033
    per traveller
    found 16 hours ago
    Casa Elena by Otium
  • Dec 31 - Jan 6

    WALD HAUS by DW + Flight

    Naguabo
    6 nights
    4.0 star property
    9.2/10 - Wonderful (11 reviews)
    "The home itself is absolutely stunning but the road to the villa is not just narrow, it's washed out in many places, we struggled to navigate the potholes even with a jeep and an SUV, I would not drive it at night. There are great amenities like the fridge and bathroom downstairs, the coffee / cocktail bar is fabulous.The kitchen was well-stocked with basic spices and supplies but it was crawling with roaches. Wifi is spotty so be sure to have the guidebook downloaded and screenshots of the..."
    Reviewed August 13, 2026
    Roundtrip • Montreal (YUL) - San Juan (SJU)
    YUL - SJU • 1 stop SJU - YUL • 2 stops
    CA $9,326
    CA $6,228
    per traveller
    found 1 day ago
    WALD HAUS by DW

Discover the most popular places to visit in Roosevelt Roads

Top Ski Roosevelt Roads Hotels

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.

Plan the ultimate ski vacation in Roosevelt Roads

What are some benefits when booking ski vacations in Roosevelt Roads?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Roosevelt Roads?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Roosevelt Roads, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Roosevelt Roads with some as cheap as CA $1,751. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Roosevelt Roads. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 40 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Roosevelt Roads.

Can I book all-inclusive ski vacations in Roosevelt Roads?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Roosevelt Roads in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Roosevelt Roads's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Roosevelt Roads?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Roosevelt Roads. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 40. With Expedia Rewards, you can earn points towards your next booking.