Title: Book the Best South Side LUXURY Hotels - Upscale Hotels in South Side, PA | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx6343590)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d6343590.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473585-South-Side-Pittsburgh.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in South Side, PA - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on South Side Luxury Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-11-02&endDate=2025-11-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-11-03&endDate=2025-11-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top South Side Luxury Hotels ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/6000000/5530000/5522800/5522759/9482fe0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5530000/5522800/5522759/9fbc5049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5530000/5522800/5522759/e4b22c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5530000/5522800/5522759/914b4807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HYATT house Pittsburgh-South Side South Side Flats 8.6/10 Excellent (1005) "Location, room, staff were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Srijon CA $189 CA $216 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Pittsburgh-Hotels-HYATT-House-Pittsburgh-South-Side.h5522759.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/76c1ea4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/81ee4892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/49924f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/a12c8351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG South Side Flats 7.2/10 Good (1030) "Great property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James H CA $116 CA $133 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Pittsburgh-South-Side.h914423.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17®ionId=6343590&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Drury Plaza Hotel Pittsburgh Downtown](//images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f_y.jpg) ### Drury Plaza Hotel Pittsburgh Downtown 10/10 Excellent "Every member of the staff went above and beyond, they were all amazing! They were all incredible! The room was really clean, we didn’t end up being able to take advantage, but the food and drinks they offer were a really nice perk! " [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![DoubleTree by Hilton Pittsburgh - Green Tree](//images.trvl-media.com/lodging/1000000/20000/12400/12343/ea79878f_y.jpg) ### DoubleTree by Hilton Pittsburgh - Green Tree 10/10 Excellent "Loved staying here! The staff was super sweet and accommodating, and checking in and out was quick and easy. Great location especially if you’re spending time downtown. Absolutely the most comfortable bed i’ve ever slept in the pillows were amazingly soft the best sleep i’ve gotten in a while! Would 100% stay here again. " [](https://expedia.ca/Pittsburgh-Hotels-Doubletree-By-Hilton-Pittsburgh-Greentree.h12343.Hotel-Information) ![Hyatt Regency Pittsburgh International Airport](//images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_y.jpg) ### Hyatt Regency Pittsburgh International Airport 10/10 Excellent "The room is very clean. They didn’t need to, but they cleaned it every day. The only problem was that it was an adjoining room to people that we weren’t connected with. And I know you can’t help this, but they were loud and rude. Before you give these rooms to customers, you should make them aware of this so that they could choose to be in a room that’s not adjoined to another room." [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information) ![La Quinta Inn by Wyndham Pittsburgh Airport](//images.trvl-media.com/lodging/1000000/10000/2500/2472/b3836cb9_y.jpg) ### La Quinta Inn by Wyndham Pittsburgh Airport 10/10 Excellent "Yes" [](https://expedia.ca/Pittsburgh-Hotels-La-Quinta-Inn-By-Wyndham-Pittsburgh-Airport.h2472.Hotel-Information) ![Hampton Inn Pittsburgh/Monroeville](//images.trvl-media.com/lodging/1000000/70000/67700/67685/d4fb34d9_y.jpg) ### Hampton Inn Pittsburgh/Monroeville 10/10 Excellent "I just like the convenience. Outback attached. " [](https://expedia.ca/Pittsburgh-Hotels-Hampton-Inn-PittsburghMonroeville.h67685.Hotel-Information) ![Pittsburgh Marriott City Center](//images.trvl-media.com/lodging/1000000/50000/43500/43447/aaf723c4_y.jpg) ### Pittsburgh Marriott City Center 10/10 Excellent "Food was very good. Room clean staff was very helpful and friendly " [](https://expedia.ca/Pittsburgh-Hotels-Marriott-Pittsburgh-City-Center-Hotel.h43447.Hotel-Information) ![Sheraton Pittsburgh Hotel at Station Square](//images.trvl-media.com/lodging/1000000/30000/20400/20319/ae616b8b_y.jpg) ### Sheraton Pittsburgh Hotel at Station Square 10/10 Excellent "Very ckean" [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.Hotel-Information) ![Wyndham Grand Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg) ### Wyndham Grand Pittsburgh Downtown 10/10 Excellent "Parking sucked super expensive " [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](//images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton 10/10 Excellent "This was a perfect place for a Pittsburgh Steelers game. Super close (walking distance) for great restaurants, sightseeing and of course the game!" 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