Title: South Shore Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $738 Expedia.ca [Hotels in South Shore](https://expedia.ca/South-Shore-Pittsburgh-Hotels.0-n553248634333002587-0.Travel-Guide-Filter-Hotels)[Flights to Pittsburgh](https://expedia.ca/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights)[Things to do in Pittsburgh](https://expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)[South Shore Car Rentals](https://expedia.ca/Car-Rentals-In-South-Shore.d553248634333002587.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248634333002587/2b17da6a-c3b2-4aff-ac99-a74d1fd9f910.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Shore Vacation Packages ## 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 ## Top Holiday Package Deals in South Shore 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 ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Pittsburgh Downtown Downtown Pittsburgh CA $894 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! (3,142 reviews) Great location and very friendly staff. The hotel lobby was nice, but the rooms are outdated, and the bathroom tub was stained yellow and red. Reviewed on Dec 8, 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 ## Where to stay in South Shore Find the best South Shore areas and neighborhoods for the activities you enjoy most. [Learn more about South Shore](https://expedia.ca/Pittsburgh-South-Shore.dx553248634333002587) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473877-Downtown-Pittsburgh.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Pittsburgh 2 out of top 10 points of interest in this area 4.5/5(187 area reviews) Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks. [Find hotel + flight trips in Downtown Pittsburgh](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Pittsburgh&DestID=6057662&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473955-North-Shore-Pittsburgh.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North Shore 2 out of top 10 points of interest in this area 4.5/5(30 area reviews) Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations. [Find hotel + flight trips in North Shore](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20Shore&DestID=553248633938969308&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Southwest Pennsylvania](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94063-The-Andy-Warhol-Museum.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North Side 1 out of top 10 points of interest in this area If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station. [Find hotel + flight trips in North Side](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20Side&DestID=891415173200363520&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Senator John Heinz History Center which includes signage and interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/41000/41929-Senator-John-Heinz-History-Center.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Strip District 4/5(1 area review) Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months. [Find hotel + flight trips in Strip District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Strip%20District&DestID=6343592&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473571-Mount-Washington-Pittsburgh.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Mount Washington Consider a visit to Ohio River Valley and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station. [Find hotel + flight trips in Mount Washington](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Mount%20Washington&DestID=6343586&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## South Shore Hotel Deals ![Sheraton Pittsburgh Hotel at Station Square](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/ae616b8b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Pittsburgh Hotel at Station Square 300 West Station Square Drive Pittsburgh PA Fully refundableReserve now, pay when you stay CA $186 CA $212 total Dec 21 - Dec 22 includes taxes & fees 8.8/10 Excellent! (1,004 reviews) Excellent view, convenient location from restaurants and incline. The room was specious and very clean. Bathroom was loaded with high quality amenities. Front desk staffs were prompt and courteous. I would recommend a city view room. Reviewed on Dec 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=20319&PinnedHotelID=20319&HadPinnedHotel=true®ionId=553248634333002587) ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Pittsburgh Downtown 600 Commonwealth Pl Pittsburgh PA Fully refundableReserve now, pay when you stay CA $161 CA $183 total Dec 28 - Dec 29 includes taxes & fees 8.2/10 Very Good! (3,210 reviews) Room was a little small Reviewed on Dec 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true®ionId=553248634333002587) ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton 453 Boulevard of the Allies Pittsburgh PA Fully refundableReserve now, pay when you stay CA $147 CA $170 total Dec 21 - Dec 22 includes taxes & fees 8.4/10 Very Good! (1,408 reviews) Great staff! Room was nice. The bars nice. Very Walkable to area restaurants & Market Square. Valet service was fast. Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=17900777&PinnedHotelID=17900777&HadPinnedHotel=true®ionId=553248634333002587) [See all 1,845 properties in South Shore](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F12%2F2025&endDate=12%2F12%2F2025®ionId=553248634333002587) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](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) ## Frequently asked questions ### How much does a South Shore vacation package cost? ### How do I get a cheap travel package to South Shore? ### Where should I stay in South Shore? ### What are the top hotels in South Shore? ### How far in advance should I book my South Shore vacation? ### What does an Expedia South Shore travel package include? ### What should I know before booking a South Shore travel package? ### Can I choose my airline with a South Shore Expedia vacation package? ### If I'm not able to travel, can I cancel my South Shore vacation package? ### Discover the most popular places to visit in South Shore ![Monongahela Incline featuring a gondola](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/41000/41782-Monongahela-Incline.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Monongahela Incline 4.5/5(22 reviews) Spectacular views of the Pittsburgh cityscape await at the top of the steepest funicular railway in the United States. [](https://expedia.ca/Monongahela-Incline-South-Shore.d6078693.Vacation-Attraction) ### Things to do ![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/fb378b65-03b5-422b-84c6-ec829fe06b75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl CA $18 per adult [](https://expedia.ca/things-to-do/pittsburgh-bar-hunt-party-through-pittsburgh-bar-crawl.a697587.activity-details) ![Make new friends as you learn the exciting history of whiskey in Pittsburgh](https://mediaim.expedia.com/localexpert/1359320/44c64494-c602-43ff-a552-b170c4986e13.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Whiskey Rebellion & Prohibition Tour CA $63 per adult [](https://expedia.ca/things-to-do/whiskey-rebellion-prohibition-tour.a1359320.activity-details) ![Pittsburgh Segway Tour ](https://mediaim.expedia.com/localexpert/49957773/c24e2781-c83a-45d9-95b4-fbb2f0c4d572.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh Segway Tour CA $82 per adult [](https://expedia.ca/things-to-do/pittsburgh-segway-tour.a49957773.activity-details) [See all activities in Pittsburgh](https://expedia.ca/things-to-do/search?rid=553248634333002587) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.