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
San Juan Antiguo
Save 100% on your flight
Price was $1,166, price is now $694 per person
$694
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (636 reviews)
The room is spacious and nice. There were 3 of us and the sleeper couch was not comfortable at all.
The water takes a while to warm up so the shower was a little on the chilly side.
The jacuzzi was dirty and didn't use which was a disappointment.
The shuttle was out of service. The Lyft was reasonable $5 to $10 for 3 of us to get to Old San Juan and the cruise port.
The staff was very friendly and helpful. They let us keep our luggage there after check out. They were there late for check in as well.
Reviewed on Apr 23, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Save 100% on your flight
Price was $1,521, price is now $963 per person
$963
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (665 reviews)
From the moment we booked this trip, the staff at the hotel were very communicative and very easy to work with. We stayed with them for our 20th wedding anniversary and they were so kind and helpful. They gave us suggestions of places to go and things to do. You could tell they were very proud of the island and what it had to offer. One note: the pool on the 4th floor was what I consider odd. Not really a pool to swim in. Although we did not take advantage of it, the sister property around the corner had a pool available for our use. We did visit the bar and had some of the best drinks, with and without alcohol. It was a very chic vibe. We felt very welcomed and taken care of. I would recommend staying here.
Reviewed on Apr 7, 2026
OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was $1,410, price is now $908 per person
$908
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (642 reviews)
Amazing time, services and facility.
Reviewed on Apr 23, 2026
Ola Boutique Hotel
Condado
Save 100% on your flight
Price was $1,760, price is now $1,144 per person
$1,144
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (775 reviews)
El personal muy amable y las instalaciones bastantante limpias
Reviewed on Apr 25, 2026
Aire de O:live
Isla Verde
Save 100% on your flight
Price was $2,123, price is now $1,382 per person
$1,382
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (518 reviews)
Beautiful hotel. I loved that it wasn't huge. I stayed for my birthday trip. The rooms were beautiful and staff was so lovely. Enjoyed my stay and can't wait to come back.
Reviewed on Apr 26, 2026
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See all available trips from Columbus to Roosevelt Roads
View all trips5* Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Hugo's Rental
Old San Juan
Price was $765, price is now $647 per person
$647
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (325 reviews)
El servicio es excelente, el cuarto muy bonito, amplio y limpio, con excelente ubicación. Si regreso a Puerto Rico definitivamente me volvería a quedar allí
Reviewed on Apr 25, 2026
Fairmont El San Juan Villa Experience
Isla Verde
Save 100% on your flight
Price was $2,722, price is now $2,058 per person
$2,058
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
7.6/10 Good! (140 reviews)
The beach was nice but the lounge chair cushions were filthy …. The casino customer service was mediocre
Reviewed on Mar 24, 2026
Condado Vanderbilt Hotel
Condado
Price was $1,146, price is now $880 per person
$880
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (1,707 reviews)
Such a pleasure to stay at the hotel. The staff was so lovely and welcoming. Location and amenities were perfect for our trip.
Reviewed on Apr 24, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips3 Night Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,134, price is now $724 per person
$724
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (636 reviews)
The room is spacious and nice. There were 3 of us and the sleeper couch was not comfortable at all.
The water takes a while to warm up so the shower was a little on the chilly side.
The jacuzzi was dirty and didn't use which was a disappointment.
The shuttle was out of service. The Lyft was reasonable $5 to $10 for 3 of us to get to Old San Juan and the cruise port.
The staff was very friendly and helpful. They let us keep our luggage there after check out. They were there late for check in as well.
Reviewed on Apr 23, 2026
Aire de O:live
Isla Verde
Save 100% on your flight
Price was $1,362, price is now $898 per person
$898
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (518 reviews)
Beautiful hotel. I loved that it wasn't huge. I stayed for my birthday trip. The rooms were beautiful and staff was so lovely. Enjoyed my stay and can't wait to come back.
Reviewed on Apr 26, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Save 100% on your flight
Price was $1,248, price is now $829 per person
$829
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (665 reviews)
From the moment we booked this trip, the staff at the hotel were very communicative and very easy to work with. We stayed with them for our 20th wedding anniversary and they were so kind and helpful. They gave us suggestions of places to go and things to do. You could tell they were very proud of the island and what it had to offer. One note: the pool on the 4th floor was what I consider odd. Not really a pool to swim in. Although we did not take advantage of it, the sister property around the corner had a pool available for our use. We did visit the bar and had some of the best drinks, with and without alcohol. It was a very chic vibe. We felt very welcomed and taken care of. I would recommend staying here.
Reviewed on Apr 7, 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.
Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,166, price is now $694 per person
$694
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (636 reviews)
The room is spacious and nice. There were 3 of us and the sleeper couch was not comfortable at all.
The water takes a while to warm up so the shower was a little on the chilly side.
The jacuzzi was dirty and didn't use which was a disappointment.
The shuttle was out of service. The Lyft was reasonable $5 to $10 for 3 of us to get to Old San Juan and the cruise port.
The staff was very friendly and helpful. They let us keep our luggage there after check out. They were there late for check in as well.
Reviewed on Apr 23, 2026
Paradise Villas & Vacations
Cerro Gordo
Price was $1,566, price is now $989 per person
$989
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
10/10 Exceptional! (11 reviews)
Alex was great to answer all our questions and concerns
We did have a couple issues with the fride hamdle.and the dront of a drawer falling off and there was hair and sand.in a couple bed drawers, but besides that the place was beautiful.
Reviewed on Feb 23, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Save 100% on your flight
Price was $1,521, price is now $963 per person
$963
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (665 reviews)
From the moment we booked this trip, the staff at the hotel were very communicative and very easy to work with. We stayed with them for our 20th wedding anniversary and they were so kind and helpful. They gave us suggestions of places to go and things to do. You could tell they were very proud of the island and what it had to offer. One note: the pool on the 4th floor was what I consider odd. Not really a pool to swim in. Although we did not take advantage of it, the sister property around the corner had a pool available for our use. We did visit the bar and had some of the best drinks, with and without alcohol. It was a very chic vibe. We felt very welcomed and taken care of. I would recommend staying here.
Reviewed on Apr 7, 2026
Don't see what you're looking for?
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 $647. 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 $647. 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.
