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Roosevelt Roads Ski Holidays

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Top Ski holiday packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • 19 Dec - 26 Dec

    La Calma Poshtel + Flight

    Santurce
    6 nights
    2.0 star property
    7.2/10 - Good (912 reviews)
    "The room was clean. The door to my room had been tampered with, I reached out to the owner and there was something’s missing from my room. They had stated that it was the housekeeper but that did not make sense to me as they should have the key/code. I ended my stay a few days earlier because I did not feel safe in that area, which I do let the rental company know."
    Reviewed November 10, 2026
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,524
    £1,384
    per traveller
    found 1 day ago
    La Calma Poshtel
  • 2 Jan - 8 Jan

    El Conquistador Resort + Flight

    Cabezas
    6 nights
    4.0 star property
    9.2/10 - Wonderful (3,698 reviews)
    "Huge property, lots of good restaurants."
    Reviewed November 10, 2026
    Return • London (LON) - San Juan (SJU)
    LGW - SJU • 1 stop SJU - LHR • 1 stop
    £2,270
    £1,849
    per traveller
    found 7 hours ago
    El Conquistador Resort
  • 19 Dec - 26 Dec

    Hyatt Vacation Club at Hacienda del Mar, Dorado + Flight

    Sabana
    6 nights
    3.5 star property
    9.4/10 - Exceptional (4,217 reviews)
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £2,129
    £1,990
    per traveller
    found 1 day ago
    Hyatt Vacation Club at Hacienda del Mar, Dorado
  • 19 Dec - 26 Dec

    The Fox Hotel + Flight

    Ponce Centro
    6 nights
    3.5 star property
    7.2/10 - Good (1,008 reviews)
    "The hot water never works, the sheets and fitted were dirty."
    Reviewed November 10, 2026
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,526
    £1,441
    per traveller
    found 1 day ago
    The Fox Hotel
  • 28 Dec - 3 Jan

    Olimpo Hotel & Suites + Flight

    Santurce
    6 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Estaba muy limpio y acogedor excelente lugar para quedarse lo recomendaria a mis amigo"
    Reviewed November 9, 2026
    Return • London (LON) - San Juan (SJU)
    LHR - SJU • 1 stop SJU - LGW • 1 stop
    £2,063
    £1,966
    per traveller
    found 10 hours ago
    Olimpo Hotel & Suites

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.

Planning your Roosevelt Roads ski holiday

How can I book the best ski holiday to Roosevelt Roads in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Roosevelt Roads. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.

How can I find cheap Roosevelt Roads ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Roosevelt Roads accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £1,384. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Roosevelt Roads?

Use our handy last-minute deals page to look for ski holidays to Roosevelt Roads at a steal. If your dates are fixed, simply input the details and see what specials are available.

What should I consider when booking family ski holidays in Roosevelt Roads?

Roosevelt Roads is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.

Can I book all-inclusive ski holidays to Roosevelt Roads?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Roosevelt Roads. If not, consider booking your flights and accommodation together to save money that way instead.

When's the best time of year to plan a ski trip to Roosevelt Roads?

Ski season in Roosevelt Roads generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.

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

If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.

Can I book a Roosevelt Roads ski trip with free cancellation and/or flexible dates?

If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Roosevelt Roads that offer it.

Why should I book a ski holiday package in Roosevelt Roads with Expedia?

Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.