Title: Book the Best HISTORIC Hotels in South Side in 2026 | 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) ![South Side Flats showing a garden](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in South Side, PA from CA $176 - ![](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 Historic Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side historic hotels ![Lobby](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/d4b2262e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/862fa148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/3e1b675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/8dc88ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel Pittsburgh Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) Downtown Pittsburgh 9.4/10 Exceptional (2144) "Great hotel, super friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacques CA $164 CA $187 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![Room, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/b0ce2278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/5c6f68cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking (One-Bedroom Suite)](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/e5119a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/d791efd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Grand Pittsburgh Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) Downtown Pittsburgh 8.2/10 Very good (3263) "Very nice place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CAROLYN CA $159 CA $181 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/7eb3a999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/59c89368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/w2227h2817x0y3-6caf03aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/2eeadb12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni William Penn Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) Downtown Pittsburgh 9.2/10 Wonderful (1835) "The staff were friendly and the decorations were lovely. Great room and location, will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Saundra CA $213 CA $243 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/26288e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/52305043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/14fa516b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/82a41eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Pittsburgh Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-Homewood-Suites-By-Hilton-Pittsburgh-Downtown.h12435017.Hotel-Information) Downtown Pittsburgh 9.2/10 Wonderful (1472) "Loved the breakfast and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $179 CA $204 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Homewood-Suites-By-Hilton-Pittsburgh-Downtown.h12435017.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/5c026a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/99ca3c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/cf059c81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/05005561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Pittsburgh-Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-Hampton-Inn-Suites-Pittsburgh-Downtown.h1668434.Hotel-Information) Downtown Pittsburgh 9.4/10 Exceptional (1305) "This place is great! Close to everything, very clean and well maintained. Super friendly front desk. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) melissa CA $160 CA $182 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Pittsburgh-Hotels-Hampton-Inn-Suites-Pittsburgh-Downtown.h1668434.Hotel-Information) ![Banquet hall](https://images.trvl-media.com/lodging/59000000/59000000/58991300/58991282/173e10d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/59000000/59000000/58991300/58991282/2254bb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/59000000/59000000/58991300/58991282/bb9b3a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/59000000/59000000/58991300/58991282/86c4d5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Abode Pittsburgh - Downtown Convention Center [](https://www.expedia.ca/Pittsburgh-Hotels-Abode-The-Pennsylvanian-1-Bedroom-Suite.h58991282.Hotel-Information) Downtown Pittsburgh 7.6/10 Good (87) "Good location, clean place. Was affordable. Perfect for our guys weekend, with the 3 of us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $66 CA $214 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Abode-The-Pennsylvanian-1-Bedroom-Suite.h58991282.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/a3d9d02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/bea283f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/65ee55fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Pittsburgh, a Marriott Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-The-Westin-Pittsburgh.h14295.Hotel-Information) Downtown Pittsburgh 8.6/10 Excellent (1001) "Large, comfortable hotel that is conveniently located downtown and next door to the convention center." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raman CA $221 CA $252 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Westin-Pittsburgh.h14295.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/149df966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/8644429c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/62d6f503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Placemakr Downtown Pittsburgh at The Pennsylvanian [](https://www.expedia.ca/Pittsburgh-Hotels-Placemakr-Downtown-Pittsburgh.h114312743.Hotel-Information) Downtown Pittsburgh 8.0/10 Very good (46) "I had a wonderful stay, very quiet and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $183 CA $209 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Placemakr-Downtown-Pittsburgh.h114312743.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/389f6f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/be7d1b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/cc107db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/e272b510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Pittsburgh Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-Renaissance-Pittsburgh-Hotel.h581071.Hotel-Information) Downtown Pittsburgh 9.0/10 Wonderful (1005) "Spotless room, great beds & linens, friendly and attentive staff. Loved the ambiance and vibe of Braddock's Rebellion too. Will definitely stay at the Renaissance Pittsburgh again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DARCEE CA $232 CA $265 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Pittsburgh-Hotels-Renaissance-Pittsburgh-Hotel.h581071.Hotel-Information) ![Breakfast served, Modern European cuisine](https://images.trvl-media.com/lodging/28000000/27050000/27042200/27042182/09d42e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/28000000/27050000/27042200/27042182/9ecef224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/28000000/27050000/27042200/27042182/6f4f0c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27050000/27042200/27042182/c57d969c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel Pittsburgh Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-AC-Hotel-Pittsburgh-Downtown.h27042182.Hotel-Information) Downtown Pittsburgh 8.8/10 Excellent (638) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michaela CA $154 CA $176 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Pittsburgh-Hotels-AC-Hotel-Pittsburgh-Downtown.h27042182.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=2026-01-01&endDate=2026-01-02®ionId=6343590&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg) ### Wyndham Grand Pittsburgh Downtown 10/10 Excellent "Very nice place to stay!" [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Kimpton Hotel Monaco Pittsburgh by IHG](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df_y.jpg) ### Kimpton Hotel Monaco Pittsburgh by IHG 10/10 Excellent "Super cool hotel with friendly staff. They served hot cocoa on check in, and have a cocktail hour from 5 - 6 pm complimentary. There is also coffee service in the morning complementary. We loved it. " [](https://expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.Hotel-Information) ![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6_y.jpg) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown 10/10 Excellent "Great stay! Will be back!" [](https://expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.Hotel-Information) ![Drury Plaza Hotel Pittsburgh Downtown](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f_y.jpg) ### Drury Plaza Hotel Pittsburgh Downtown 10/10 Excellent "Wonderful staff, clean room and amenities are great" [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![Hyatt House Pittsburgh/Bloomfield/Shadyside](https://images.trvl-media.com/lodging/10000000/9710000/9708000/9707925/f987c707_y.jpg) ### Hyatt House Pittsburgh/Bloomfield/Shadyside 10/10 Excellent "Always a great stay, great staff." [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-House-PittsburghBloomfieldShadyside.h9707925.Hotel-Information) ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg) ### Omni William Penn Hotel 10/10 Excellent "Amazing, as always!!" [](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![Hilton Garden Inn Pittsburgh Downtown](https://images.trvl-media.com/lodging/10000000/9380000/9378100/9378026/c02cf3a6_y.jpg) ### Hilton Garden Inn Pittsburgh Downtown 10/10 Excellent "The perfect hotel when visiting Pittsburgh! " [](https://expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-Downtown.h9378026.Hotel-Information) ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton 10/10 Excellent "Yes!" [](https://expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.Hotel-Information) ![Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/76c1ea4b_y.jpg) ### Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG 10/10 Excellent "Very convenient location " [](https://expedia.ca/Pittsburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Pittsburgh-South-Side.h914423.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Pittsburgh ](https://www.expedia.ca/4Star-Pittsburgh-Hotels.s40-0-d601717.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Arlington ](https://www.expedia.ca/5Star-Arlington-Pittsburgh-Hotels.s50-n804081383557210112-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Knoxville ](https://www.expedia.ca/5Star-Knoxville-Pittsburgh-Hotels.s50-n804083795867832320-0.Travel-Guide-Filter-Hotels) - 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