Title: Book the Best HISTORIC Hotels in South Side in 2025 | 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 Historic 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 Historic Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Historic Hotels ![Property amenity](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f.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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/5f06b9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/20aec4f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel Pittsburgh Downtown Downtown Pittsburgh 9.6/10 Exceptional (2089) "Great staff and breakfast. We had a great stay." CA $167 CA $191 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/7eb3a999.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/6b9a15fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni William Penn Hotel Downtown Pittsburgh 9.0/10 Wonderful (1731) "Great Stay. " CA $235 CA $268 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![Premium Deluxe Suite, 1 Bedroom, 2 Queen Beds | Living area](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/48a1d3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/d05de413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Homewood Suites by Hilton Pittsburgh Downtown Downtown Pittsburgh 9.2/10 Wonderful (1402) "Spacious clean room, good continental breakfast, friendly staff." CA $184 CA $210 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Pittsburgh-Hotels-Homewood-Suites-By-Hilton-Pittsburgh-Downtown.h12435017.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/5ee535dd.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/500891cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Grand Pittsburgh Downtown Downtown Pittsburgh 8.2/10 Very good (3087) "Great location Great hotel " CA $218 CA $249 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/96b7ccf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/208098d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/w3839h2506x0y12-4fe72711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/adbecbcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Pittsburgh-Downtown Downtown Pittsburgh 9.4/10 Exceptional (1307) "Very nice location and clean rooms. Breakfast was convenient and good. " CA $198 CA $226 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsburgh-Hotels-Hampton-Inn-Suites-Pittsburgh-Downtown.h1668434.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/59000000/59000000/58991300/58991282/ce3d7055.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/59000000/59000000/58991300/58991282/0c6108dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Abode Pittsburgh - Downtown Convention Center Downtown Pittsburgh 7.6/10 Good (82) "Location nice" CA $73 CA $242 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Pittsburgh-Hotels-Abode-The-Pennsylvanian-1-Bedroom-Suite.h58991282.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/c173f17f.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) ![Premium Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/acad0b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/54a4e2a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh 7.8/10 Good (26) "Thank you Josh for helping us with our second reservation. The hotel is elegant with old school charm. The suites has washer/ dryers and full kitchen and very friendly to us bicyclists " CA $187 CA $213 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pittsburgh-Hotels-Placemakr-Downtown-Pittsburgh.h114312743.Hotel-Information) ![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) ![37-inch LCD TV with cable channels, Smart TV, Netflix](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/78dd34ad.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581100/581071/389f6f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Pittsburgh Hotel Downtown Pittsburgh 9.0/10 Wonderful (1010) "Great hotel in Pittsburgh." CA $261 CA $298 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsburgh-Hotels-Renaissance-Pittsburgh-Hotel.h581071.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74740000/74738500/74738428/43c9bf5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74740000/74738500/74738428/0f1b9869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74740000/74738500/74738428/d529037c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/75000000/74740000/74738500/74738428/3c7fef58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern All-New, Near Downtown, Private Parking - walking to Children Hospital Garfield 10/10 Exceptional (55) "Frank was great to work with and his place was just as advertised. It looked brand new inside and everything was very clean. The beds were very comfortable, bathrooms looked brand new, and the location was perfect. We would certainly stay there again!" CA $185 CA $504 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Pittsburgh-Hotels-Modern-All-New-3-Bedroom-35-Bath-Private-Parking-Walking-To-Children-Hospital.h74738428.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/18ddf67f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/0b0754bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/516c0c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Pittsburgh, a Marriott Hotel Downtown Pittsburgh 8.6/10 Excellent (1004) "It's an excellent hotel in an excellent locale." CA $264 CA $301 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Westin-Pittsburgh.h14295.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=2025-10-30&endDate=2025-10-31®ionId=6343590&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Wyndham Grand Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg) ### Wyndham Grand Pittsburgh Downtown 10/10 Excellent "The buffet foods were cold. " [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG](//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 "This is our third time coming to this hotel, and it has always been clean and the breakfast has been good and I feel safe" [](https://expedia.ca/Pittsburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Pittsburgh-South-Side.h914423.Hotel-Information) ![Hilton Garden Inn Pittsburgh Downtown](//images.trvl-media.com/lodging/10000000/9380000/9378100/9378026/c02cf3a6_y.jpg) ### Hilton Garden Inn Pittsburgh Downtown 10/10 Excellent "Clean , a lot of new people working so slow but friendly " [](https://expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-Downtown.h9378026.Hotel-Information) ![Omni William Penn Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg) ### Omni William Penn Hotel 10/10 Excellent "Yes, we had an awesome time " [](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![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 "Nice hotel with friendly staff. I enjoyed the free breakfasts and dinners. " [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6_y.jpg) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown 10/10 Excellent "Great hotel" [](https://expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.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 "Nice location parking little hard lot always full" [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.Hotel-Information) ![Hilton Garden Inn Pittsburgh University Place](//images.trvl-media.com/lodging/1000000/120000/119000/118998/6c759b6f_y.jpg) ### Hilton Garden Inn Pittsburgh University Place 10/10 Excellent "Very safe place," [](https://expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-University-Place.h118998.Hotel-Information) ![Homewood Suites by Hilton Pittsburgh Downtown](//images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/48a1d3a1_y.jpg) ### Homewood Suites by Hilton Pittsburgh Downtown 10/10 Excellent "Enjoyed my stay. Parking over priced." 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