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.
Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
$840
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (748 reviews)
Ola Boutique Hotel

Ola Boutique Hotel

Condado
Save 100% on your flight
$1,464
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (1,019 reviews)
The lobby and lounge were very quaint and the staff that greeted us the 1st night was kind. Our room was spacious - we were 4 . The bedrooms were roomy and the showers were great. The closets were large but only one had shelves and a basket to store our belongings. The property is nestled in a very tight spot on a 2 lane street that is very busy. One of the housekeepers stopped traffic for us so that we could reverse out of the parking spot. I did not catch her name but she was on duty Tuesday efternoon. Please thank her again! The parking…….is not good! The spots are limited and in the morning blocked by cars that made it very challenging to exit. Fortunately , the amazing staff was ready to assist. Chris especially went above and beyond to ensure we had a spot when we arrived. He helped us 2 nights without hesitation and with a smile on his face. Thank you Chris! I met Elliott in the am. He was very welcoming and cooked some delicious eggs to go with my complementary continental breakfast. Parking is the reason my rating is not higher. It was a challenge each time we entered and exited the lot. The staff was super helpful each time however I would’ve preferred to not worry about parking. Thank you again to the very kind and helpful staff! They really are a great team!

Reviewed on Oct 26, 2026

Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
Save 100% on your flight
$5,441
per person
Dec 29 - Jan 2
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

WALD HAUS by DW

WALD HAUS by DW

$2,346
per person
Dec 9 - Dec 13
found 8 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

Margaritaville Vacation Club by Wyndham - Rio Mar

Margaritaville Vacation Club by Wyndham - Rio Mar

Mameyes II
$1,701
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (308 reviews)
it’s an unbelievable property, everyone is extremely kind everything is well done. it was a life changing trip

Reviewed on Oct 20, 2026

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5* Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
$1,540
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.4/10 Exceptional! (1,857 reviews)
Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
Save 100% on your flight
$5,441
per person
Dec 29 - Jan 2
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

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II
Save 100% on your flight
$3,363
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (2,275 reviews)
Realmente una estadía maravillosa

Reviewed on Oct 25, 2026

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3 Night Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
Save 100% on your flight
$682
per person
Jan 3 - Jan 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
8.8/10 Excellent! (748 reviews)
Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
$4,456
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

Ola Boutique Hotel

Ola Boutique Hotel

Condado
$1,154
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (1,019 reviews)
The lobby and lounge were very quaint and the staff that greeted us the 1st night was kind. Our room was spacious - we were 4 . The bedrooms were roomy and the showers were great. The closets were large but only one had shelves and a basket to store our belongings. The property is nestled in a very tight spot on a 2 lane street that is very busy. One of the housekeepers stopped traffic for us so that we could reverse out of the parking spot. I did not catch her name but she was on duty Tuesday efternoon. Please thank her again! The parking…….is not good! The spots are limited and in the morning blocked by cars that made it very challenging to exit. Fortunately , the amazing staff was ready to assist. Chris especially went above and beyond to ensure we had a spot when we arrived. He helped us 2 nights without hesitation and with a smile on his face. Thank you Chris! I met Elliott in the am. He was very welcoming and cooked some delicious eggs to go with my complementary continental breakfast. Parking is the reason my rating is not higher. It was a challenge each time we entered and exited the lot. The staff was super helpful each time however I would’ve preferred to not worry about parking. Thank you again to the very kind and helpful staff! They really are a great team!

Reviewed on Oct 26, 2026

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See all available trips from Columbus to Roosevelt Roads
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4 Night Ski vacations in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
63 Bay View by Otium

63 Bay View by Otium

Palmas
$1,025
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to San Juan (SJU)
5/10 (4 reviews)
The sealant under the shower door was coming off, causing water to leak out. pull out couch was broken and due to it being broken I did not lift it to look for the remote that was stuck underneath. Came back one day and the door was wide open. Horrible communication. Uber and door dash could never find us. Not happy with my stay at ALL

Reviewed on Jun 15, 2026

Ola Boutique Hotel

Ola Boutique Hotel

Condado
Save 100% on your flight
$1,464
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (1,019 reviews)
The lobby and lounge were very quaint and the staff that greeted us the 1st night was kind. Our room was spacious - we were 4 . The bedrooms were roomy and the showers were great. The closets were large but only one had shelves and a basket to store our belongings. The property is nestled in a very tight spot on a 2 lane street that is very busy. One of the housekeepers stopped traffic for us so that we could reverse out of the parking spot. I did not catch her name but she was on duty Tuesday efternoon. Please thank her again! The parking…….is not good! The spots are limited and in the morning blocked by cars that made it very challenging to exit. Fortunately , the amazing staff was ready to assist. Chris especially went above and beyond to ensure we had a spot when we arrived. He helped us 2 nights without hesitation and with a smile on his face. Thank you Chris! I met Elliott in the am. He was very welcoming and cooked some delicious eggs to go with my complementary continental breakfast. Parking is the reason my rating is not higher. It was a challenge each time we entered and exited the lot. The staff was super helpful each time however I would’ve preferred to not worry about parking. Thank you again to the very kind and helpful staff! They really are a great team!

Reviewed on Oct 26, 2026

Signature Collection at Rio Mar

Signature Collection at Rio Mar

Mameyes II
Save 100% on your flight
$5,441
per person
Dec 29 - Jan 2
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?

Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $682. 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 $682. 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.