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.
310Guest-House LaVida

310Guest-House LaVida

Old San Juan
$960
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (58 reviews)
The location was great! The unit is nice, overall. Staff was accommodating and very friendly,

Reviewed on Aug 10, 2026

WALD HAUS by DW

WALD HAUS by DW

$2,604
per person
Dec 14 - Dec 20
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

Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
$5,654
per person
Dec 28 - Jan 1
found 1 day 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

APT by DW

APT by DW

Santurce
$1,091
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.8/10 Exceptional! (110 reviews)
PAZ by DW

PAZ by DW

Santurce
$1,052
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (28 reviews)
Loved the property. Absolutely beautiful.

Reviewed on Sep 11, 2026

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5* Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Hugo's Rental

Hugo's Rental

Old San Juan
$820
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (343 reviews)
Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
$5,654
per person
Dec 28 - Jan 1
found 1 day 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

Fairmont El San Juan Villa Experience

Fairmont El San Juan Villa Experience

Isla Verde
Save 100% on your flight
$1,581
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
7.8/10 Good! (157 reviews)
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3 Night Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Don Rafa Boutique Hotel & Residences

Don Rafa Boutique Hotel & Residences

Santurce
$675
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.4/10 Exceptional! (539 reviews)
Excelente

Reviewed on Oct 2, 2026

Ola Boutique Hotel

Ola Boutique Hotel

Condado
Save 100% on your flight
$676
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (980 reviews)
WALD HAUS by DW

WALD HAUS by DW

Save 100% on your flight
$1,633
per person
Dec 3 - Dec 6
found 4 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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4 Night Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
WALD HAUS by DW

WALD HAUS by DW

Save 100% on your flight
$1,506
per person
Nov 7 - Nov 11
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

Villa Azure Ocean Suites

Villa Azure Ocean Suites

Santurce
$3,074
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (3 reviews)
We had such an amazing time at Villa Azure! Our group of 16 couldn’t get enough of the gorgeous ocean views, and the fact that the beach was just a short walk away was perfect. The house itself was super cozy and beautifully decorated—plenty of space for everyone but still felt like home. We spent hours relaxing by the pool and enjoying the outdoor area, which was perfect for hanging out together. We can’t wait to come back!

Reviewed on Oct 21, 2024

Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
$5,654
per person
Dec 28 - Jan 1
found 1 day 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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Planning 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 $675. 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 $675. 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.