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.
SELVA by DW
Pitahaya
Price was $5,464, price is now $3,376 per person
$3,376
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (3 reviews)
Todo estuvo perfecto limpieza 💯communication al 💯 y los servicios ofrecido todo me parecio exelente buen olor en las toallas y sabanas ,
Reviewed on Jun 25, 2026
WALD HAUS by DW
Price was $3,839, price is now $2,456 per person
$2,456
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
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 phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
Hyatt Regency Grand Reserve Puerto Rico
Zarzal
Price was $2,044, price is now $1,420 per person
$1,420
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (3,497 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 on Nov 11, 2026
Signature Collection at Rio Mar
Mameyes II
Save 100% on your flight
Price was $6,293, price is now $4,404 per person
$4,404
per person
Jan 25 - Jan 29
found 7 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
6/10 (1 review)
Everything is 10 times more expensive compare to any other place I visites
Reviewed on Aug 8, 2026
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View all trips5* Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Four Seasons Resort and Residences Puerto Rico
Herreras
Save 100% on your flight
Price was $3,732, price is now $2,929 per person
$2,929
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.4/10 Exceptional! (57 reviews)
We made it our mission to use every amenity this Four Seasons offers, and somehow the property delivered on all of them.
We started our days at the breakfast buffet ($52). The spread was incredible, but the real star was the passion fruit juice. I'm not exaggerating when I say I had three glasses every single morning.
From there we kept busy. We played tennis, hit balls at the driving range, and took a cart around the golf course. We tried both swimming pools, which were spotless, and spent time on a beach with some of the softest sand we've ever walked on. We borrowed bikes and rode the trails down to the farm, the animal sanctuary, and the petting zoo, which was a highlight. We also spent time at the wellness center, which was the perfect way to slow down between activities.
One of the best parts was how uncrowded everything felt. There were so few guests that the pools, beach, and courts felt almost private. And whenever we needed to get somewhere, a golf cart was ready to take us anywhere on the property at a moment's notice.
Dinner was just as memorable. We tried the new restaurant, Perla, and it was awesome. But Palm Court absolutely blew our minds. If you only have one dinner here, or even three, make it Palm Court.
Of course, the legendary Four Seasons concierge lived up to the reputation. Every request was handled quickly and with genuine warmth.
To sum it up in one word: iconic.
Reviewed on Nov 1, 2026
Signature Collection at Rio Mar
Mameyes II
Save 100% on your flight
Price was $6,293, price is now $4,404 per person
$4,404
per person
Jan 25 - Jan 29
found 7 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
6/10 (1 review)
Everything is 10 times more expensive compare to any other place I visites
Reviewed on Aug 8, 2026
Residences at Dorado Beach, a Ritz-Carlton Reserve
Higuillar
Price was $23,300, price is now $18,200 per person
$18,200
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.
Reviewed on Sep 1, 2025
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View all trips3 Night Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Beach Front Amapola SeaSide Apt
Isla Verde
Price was $1,827, price is now $1,331 per person
$1,331
per person
Jan 17 - Jan 20
found 14 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (9 reviews)
Host was amazing and very knowledgeable. The view was breathtaking and was only a 5 min walk to the beach. Will definitely come back!!
Reviewed on Nov 2, 2026
SELVA by DW
Pitahaya
Save 100% on your flight
Price was $4,038, price is now $2,514 per person
$2,514
per person
Feb 5 - Feb 8
found 15 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
10/10 Exceptional! (3 reviews)
Todo estuvo perfecto limpieza 💯communication al 💯 y los servicios ofrecido todo me parecio exelente buen olor en las toallas y sabanas ,
Reviewed on Jun 25, 2026
WALD HAUS by DW
Save 100% on your flight
Price was $2,773, price is now $1,771 per person
$1,771
per person
Feb 5 - Feb 8
found 15 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
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 phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips4 Night Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking
Isla Verde
Price was $1,678, price is now $774 per person
$774
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (7 reviews)
Super nice place to stay at Isla Verde. Owner was super friendly and the place is clean,, a lot of space with included kitchen and wash/drying machine. Would consider again for sure.
Reviewed on Oct 5, 2026
WALD HAUS by DW
Price was $3,080, price is now $1,928 per person
$1,928
per person
Jan 31 - Feb 4
found 3 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
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 phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
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See all available trips from Columbus to Roosevelt Roads
View all tripsPlanning your Roosevelt Roads ski vacation
What are some things I should consider when booking a Roosevelt Roads 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 Roosevelt Roads ski packages?
Right now, ski trips start at just $774. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Roosevelt Roads?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Roosevelt Roads. 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 Roosevelt Roads cost?
Sensational ski trips to Roosevelt Roads start from $774. 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 Roosevelt Roads?
The best time to hit the slopes in Roosevelt Roads 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 Roosevelt Roads 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 Roosevelt Roads 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 Roosevelt Roads with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Roosevelt Roads ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.