Title: Ski Vacations in South Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 South Side Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Pittsburgh - Green Tree](https://images.trvl-media.com/lodging/1000000/20000/12400/12343/ea79878f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Pittsburgh - Green Tree CA $720 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 8.2/10 Very Good! (1,004 reviews) The hotel was nice. Staff courteous and welcoming. Had a great experience. Room was clean. Cleaning staff was nice. Reviewed on Dec 9, 2025 ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton Downtown Pittsburgh CA $738 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 8.4/10 Very Good! (1,385 reviews) clean and comfortable! Reviewed on Dec 8, 2025 ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh CA $940 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 7.6/10 Good! (37 reviews) Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay. Reviewed on Dec 9, 2025 ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni William Penn Hotel Downtown Pittsburgh CA $867 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 9.2/10 Wonderful! (1,767 reviews) Wonderful staff and accommodations..great location especially if you plan on attending something at PPG arena Reviewed on Dec 9, 2025 ![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Pittsburgh, a Marriott Hotel Downtown Pittsburgh CA $889 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 8.6/10 Excellent! (1,003 reviews) Nice hotel in downtown Pittsburgh. Room and common area were clean and well maintained. Reviewed on Dec 8, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton Downtown Pittsburgh CA $738 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 8.4/10 Very Good! (1,385 reviews) clean and comfortable! Reviewed on Dec 8, 2025 ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh CA $940 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 7.6/10 Good! (37 reviews) Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay. Reviewed on Dec 9, 2025 ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni William Penn Hotel Downtown Pittsburgh CA $867 per person Feb 20 - Feb 23 found 1 hour ago Roundtrip non-stop flight included Montreal (YUL) to Pittsburgh (PIT) 9.2/10 Wonderful! (1,767 reviews) Wonderful staff and accommodations..great location especially if you plan on attending something at PPG arena Reviewed on Dec 9, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in South Side #### What are some benefits when booking ski vacations in South Side? 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 South Side? 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 South Side, 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 South Side with some as cheap as CA $720\. 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 South Side. 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 15 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 South Side. #### Can I book all-inclusive ski vacations in South Side? 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 South Side 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 South Side'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 South Side? 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 South Side. 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 15\. 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 South Side ](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[ South Side Hotels ](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[ South Side Vacation Rentals ](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[ South Side Car Rentals ](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)[ South Side Vacations ](https://expedia.ca/South-Side.d6343590.Destination-Travel-Guides)[ Things to do in South Side ](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities) \* 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