Title: South Shore Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $589 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 $589 per person Mar 6 - Mar 9 found 1 hour ago Roundtrip flight included Halifax (YHZ) to Pittsburgh (PIT) 8.4/10 Very Good! (1,385 reviews) Great location in downtown . Clean room . It was quiet . Good price. Reviewed on Dec 16, 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 $766 per person Mar 6 - Mar 9 found 1 hour ago Roundtrip flight included Halifax (YHZ) 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 ![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 $844 per person Mar 6 - Mar 9 found 1 hour ago Roundtrip flight included Halifax (YHZ) 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 $618 per person Mar 6 - Mar 9 found 1 hour ago Roundtrip flight included Halifax (YHZ) to Pittsburgh (PIT) 8.2/10 Very Good! (3,142 reviews) Clean and friendly staff very helpful if you're not familiar with the area Reviewed on Dec 16, 2025 ![Hotel Indigo Pittsburgh East Liberty by IHG](https://images.trvl-media.com/lodging/10000000/9040000/9032700/9032700/112ecec9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo Pittsburgh East Liberty by IHG East Liberty CA $632 per person Mar 6 - Mar 9 found 1 hour ago Roundtrip flight included Halifax (YHZ) to Pittsburgh (PIT) 8/10 Very Good! (1,003 reviews) Staff was very nice , room was very large , could have been cleaner . But a very good value , plenty of on street parking . Bar was mediocre. But good area . Reviewed on Dec 17, 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 Ross Park Mall 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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shadyside Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible. [Find hotel + flight trips in Shadyside](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Shadyside&DestID=6156339&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) ## 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 $185 CA $210 total Dec 21 - Dec 22 includes taxes & fees 8.8/10 Excellent! (1,001 reviews) Room was very clean and location was exceptional we walked bridge into city so close and close to the i cline and the boat trips Reviewed on Dec 9, 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 $179 CA $204 total Dec 18 - Dec 19 includes taxes & fees 8.2/10 Very Good! (3,235 reviews) Didn’t eat breakfast. The staff was friendly and wonderful overall. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true®ionId=553248634333002587) ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni William Penn Hotel 530 William Penn Place Pittsburgh PA Fully refundableReserve now, pay when you stay CA $213 CA $243 total Dec 24 - Dec 25 includes taxes & fees 9/10 Wonderful! (1,829 reviews) Amazing, as always!! Reviewed on Dec 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=2998&PinnedHotelID=2998&HadPinnedHotel=true®ionId=553248634333002587) [See all 1,871 properties in South Shore](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%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 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 $62 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 $80 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.