Title: Ski Vacations in Roosevelt Roads 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Shannon Willitts - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Ski hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Romeo Gay Hotel Puerta de Tierra CA $1,218 per person May 5 - May 12 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (121 reviews) Friendly staff. Nice big rooms. Expansion construction going on.Property will be adding a bar. ... I'll return. Reviewed on Feb 27, 2026 ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,699 per person Apr 12 - Apr 19 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (500 reviews) First, we had no towels no hot water for two days. Entry door would not close unless you slammed it. And the walls were way too thin. You could hear noise from upstairs and surrounding rooms. Reviewed on Feb 26, 2026 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $1,812 per person May 5 - May 12 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Everything about this Hotel is amazing! Reviewed on Feb 26, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,758 per person May 5 - May 12 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) I had a high expectation for this hotel, as it is extremely beautiful online. The lobby and staff were exceptional. I gave this review 3 stars because of the lack of attention to the room. Our exterior door in the bathroom (only source of fresh air) was broken and unable to open. We called about it but nothing was done. Also, the room felt a little dirty - some shelves and walls looked dirty. Additionally, on 2 days, our room was not serviced and we needed to make a call to remedy. The hotel roof turns into a nightclub at night. We were there on opening night for dinner and the bar and ambiance were amazing. However, don't try to fall asleep any time before 2am on Friday or Saturday - the club music is so loud. And the hotel and bar are not owned by the same people so the hotel doesn't have any control over the volume. The hottub was out of commission for 2 days - kind of a bummer. Overall - this hotel has promise - but needs more attention to detail. Reviewed on Feb 23, 2026 ![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Grand Reserve Puerto Rico Zarzal CA $2,507 per person Apr 25 - Apr 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (2,764 reviews) Room service, house cleaning, front desk are very quick and attentive! Rooms are clean! Beautiful resort with a beautiful beach. Reviewed on Feb 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-28/2026-04-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/99d8d575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Hotel Isla Verde CA $1,990 per person May 5 - May 12 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.4/10 Very Good! (2,051 reviews) Amazing property and top notch service! Reviewed on Feb 27, 2026 ![Fairmont El San Juan Villa Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577147/f326ce2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Villa Experience Isla Verde CA $3,416 per person Apr 12 - Apr 19 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 7.6/10 Good! (128 reviews) Room was good but dated, toilet wouldn't stop running.. asked front dest to sweep my patio and get rid of some ants as well as clean cat hair off my lounge chair on Saturday, never seen anyone and i left on Tuesday Reviewed on Feb 26, 2026 ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Condado Vanderbilt Hotel Condado CA $2,685 per person May 20 - May 27 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Beautiful hotel, nice hotel gym. Easy access to beach from adult pool area. Reviewed on Feb 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-28/2026-04-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $746 per person Apr 20 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) First, we had no towels no hot water for two days. Entry door would not close unless you slammed it. And the walls were way too thin. You could hear noise from upstairs and surrounding rooms. Reviewed on Feb 26, 2026 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $1,062 per person Apr 20 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Everything about this Hotel is amazing! Reviewed on Feb 26, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $953 per person Apr 20 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) I had a high expectation for this hotel, as it is extremely beautiful online. The lobby and staff were exceptional. I gave this review 3 stars because of the lack of attention to the room. Our exterior door in the bathroom (only source of fresh air) was broken and unable to open. We called about it but nothing was done. Also, the room felt a little dirty - some shelves and walls looked dirty. Additionally, on 2 days, our room was not serviced and we needed to make a call to remedy. The hotel roof turns into a nightclub at night. We were there on opening night for dinner and the bar and ambiance were amazing. However, don't try to fall asleep any time before 2am on Friday or Saturday - the club music is so loud. And the hotel and bar are not owned by the same people so the hotel doesn't have any control over the volume. The hottub was out of commission for 2 days - kind of a bummer. Overall - this hotel has promise - but needs more attention to detail. Reviewed on Feb 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-28/2026-04-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,041 per person May 12 - May 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) First, we had no towels no hot water for two days. Entry door would not close unless you slammed it. And the walls were way too thin. You could hear noise from upstairs and surrounding rooms. Reviewed on Feb 26, 2026 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $1,249 per person May 12 - May 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Staff were very accommodating, friendly, and personable. Rooms were clean. Hotel is in a great location within walking distance of a lot of great restaurants. Reviewed on Feb 27, 2026 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $1,258 per person May 12 - May 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Everything about this Hotel is amazing! Reviewed on Feb 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-28/2026-04-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Roosevelt Roads #### What are some benefits when booking ski vacations in Roosevelt Roads? If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations. #### How can I book the best ski vacation in Roosevelt Roads? It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Roosevelt Roads, and think about the time of year that's best to visit. #### How can I find cheap ski vacations? Cheap ski vacations are readily available in Roosevelt Roads with some as cheap as CA $746\. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out. #### Can I book ski packages? Yes, ski packages are readily available throughout Roosevelt Roads. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 37 when you book your accommodation and your flight together. #### What should I consider when booking family ski vacations? The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Roosevelt Roads. #### Can I book all-inclusive ski vacations in Roosevelt Roads? Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Roosevelt Roads in advance. #### What's the best time of year to plan a ski trip? The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Roosevelt Roads's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high. #### How can I find the best deals on ski packages in Roosevelt Roads? When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing. #### Can I book a ski vacation that's fully refundable? Being fully refundable is a feature you'll find on several accommodation packages in Roosevelt Roads. You can even search for it explicitly using a filter for full refundability. #### Why should I book a ski vacation package with Expedia? When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 37\. With Expedia Rewards, you can earn points towards your next booking. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Ski Vacation Destinations > - [Ski vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4115/Whistler) > - [Ski vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4332/Banff) > - [Ski vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/55374/Mont-Tremblant) > - [Ski vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/8028/Jasper) > - [Ski vacations in Jackson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180006/Jackson) > - [Ski vacations in France ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/59/France) > - [Ski vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180017/Quebec) > - [Ski vacations in Queenstown ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3611/Queenstown) > - [Ski vacations in Lake Louise ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/10115/Lake-Louise) > - [Ski vacations in Nelson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6194600/Nelson) > - [Ski vacations in Kitzbuhel ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6346453/Kitzbuehel) > - [Ski vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/174/Switzerland) > - [Ski vacations in La Plagne ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6034464/La-Plagne) > - [Ski vacations in St Gervais ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3000402612/St-Gervais-Sur-Mare) > - [Ski vacations in Austria ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/11/Austria) > - [Ski vacations in Germany ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/64/Germany) > - [Ski vacations in Wengen ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6186871/Wengen) > - [Ski vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/2680/Ontario) > - [Ski vacations in Colorado ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/207/Colorado) ## More Vacations Ideas [Flights to Roosevelt Roads ](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[ Roosevelt Roads Hotels ](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[ Roosevelt Roads Vacation Rentals ](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[ Roosevelt Roads Car Rentals ](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide)[ Roosevelt Roads Vacations ](https://expedia.ca/Roosevelt-Roads.d6360451.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app