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 San Juan Antiguo CA $1,163 per person Feb 22 - Mar 1 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (121 reviews) Super convenient location, bar across the street, convenience store and liquor across the street The bar “5” across the street has pool table and Jenna games, super cool. All entrances with gate security codes, common area to work and leave suitcase before and after check in/out Very close to port and old San Juan. Isla verde and condado 10 minute drive ( if that far) We had an amazing time. We travel with family Reviewed on Dec 6, 2025 ![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 $1,358 per person Feb 22 - Mar 1 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Clean roon staff friendly and professional Reviewed on Dec 15, 2025 ![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 $1,727 per person Feb 15 - Feb 22 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (500 reviews) The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something. Reviewed on Dec 14, 2025 ![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 $2,086 per person Feb 22 - Mar 1 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (328 reviews) My girlfriend and I just stayed at this hotel and have been talking nonstop about our stay since we left there. We really enjoyed everything about it. Friendly staff and food at the pool was AMAZING. Would 100% recommend this place and will be coming again. Reviewed on Dec 16, 2025 ![Las Casitas Village at El Conquistador](https://images.trvl-media.com/lodging/92000000/91570000/91562100/91562080/7e550371_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Las Casitas Village at El Conquistador Cabezas CA $3,533 per person Mar 8 - Mar 14 found 8 hours ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (126 reviews) Everything was great Reviewed on Dec 4, 2025 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/2026-01-16/2026-01-23/?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. ![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 $2,477 per person Feb 22 - Mar 1 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Room, staff, service, ambiance, location were perfect! I'll be back! Reviewed on Dec 14, 2025 ![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 $4,080 per person Feb 15 - Feb 22 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 7.6/10 Good! (128 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on Sep 28, 2025 ![The St. Regis Bahia Beach Resort, Puerto Rico](https://images.trvl-media.com/lodging/4000000/3810000/3800200/3800119/f088cdb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Bahia Beach Resort, Puerto Rico Herreras CA $7,188 per person Mar 8 - Mar 14 found 9 hours ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Beautiful resort. We loved every minute. Reviewed on Oct 25, 2025 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/2026-01-16/2026-01-23/?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. ![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 $782 per person Feb 16 - Feb 19 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Clean roon staff friendly and professional Reviewed on Dec 15, 2025 ![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 $1,140 per person Feb 28 - Mar 3 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something. Reviewed on Dec 14, 2025 ![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 $1,152 per person Feb 16 - Feb 19 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again. Reviewed on Dec 6, 2025 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/2026-01-16/2026-01-23/?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. ![The Oliver Hotel](https://images.trvl-media.com/lodging/108000000/107090000/107083400/107083384/2b5683ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Oliver Hotel San Juan Antiguo CA $889 per person Mar 7 - Mar 11 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (50 reviews) Nothing really close by, no front staff ever on site to help with local restaurants etc no stores nearby have to Uber everywhere. Rooms have no windows no water , ice machines etc.. Reviewed on Dec 14, 2025 ![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 $1,063 per person Feb 16 - Feb 20 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Clean roon staff friendly and professional Reviewed on Dec 15, 2025 ![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 $983 per person Jan 24 - Jan 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (500 reviews) The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something. Reviewed on Dec 14, 2025 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/2026-01-16/2026-01-23/?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 $782\. 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 40 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 40\. 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