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) ![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 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 [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-31&endDate=2026-01-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-01&endDate=2026-01-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for South Side luxury hotels ![Exterior](https://images.trvl-media.com/lodging/71000000/70900000/70891100/70891071/6ac37499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70900000/70891100/70891071/a7151c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/71000000/70900000/70891100/70891071/e4bee32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/71000000/70900000/70891100/70891071/01e4524c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa South Side Pittsburgh [](https://www.expedia.ca/Pittsburgh-Hotels-Kasa-Pittsburgh-South-Side.h70891071.Hotel-Information) South Side Flats 8.2/10 Very good (106) "Location to restaurants was great. Elevator was out of order in the parking garage the whole time and had to walk the stairs twice a day. For a week we were there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $167 CA $280 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Pittsburgh-Hotels-Kasa-Pittsburgh-South-Side.h70891071.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1200/1172/a953fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/1200/1172/160cd34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/1200/1172/71af2444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1200/1172/6790627c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Pittsburgh - Cranberry [](https://www.expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Pittsburgh-Cranberry.h1172.Hotel-Information) Mars 8.8/10 Excellent (921) "My stay was ok, room and bathroom where clean, beds and pillows ok, staff polite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $157 CA $179 total includes taxes & fees Jan 9 - Jan 10 [](https://www.expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Pittsburgh-Cranberry.h1172.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/9077df2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/ac59916e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/e06dafbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton [](https://www.expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.Hotel-Information) Downtown Pittsburgh 8.4/10 Very good (1418) "We love it here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $146 CA $169 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/6d3246bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed (Fifth Avenue House)](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/17d03475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/2df82a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/ee73444e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansions on Fifth Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information) Shadyside 8.8/10 Excellent (1000) "Beautiful place. Thank you " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ryan [](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/7bfc4a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/d16797fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/a4f9b262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/52d04c8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaklander Hotel, Autograph Collection [](https://www.expedia.ca/Pittsburgh-Hotels-The-Oaklander-Hotel.h28852483.Hotel-Information) Oakland 9.2/10 Wonderful (730) "Great Stay Overall, would recommend for anyone who is visiting Pittsburgh… " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peris J CA $279 CA $319 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Oaklander-Hotel.h28852483.Hotel-Information) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/24000000/23360000/23356700/23356627/0579f884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23360000/23356700/23356627/499ab787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23360000/23356700/23356627/a7a9953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/24000000/23360000/23356700/23356627/0ca4f109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### EVEN Hotel Pittsburgh Downtown by IHG [](https://www.expedia.ca/Pittsburgh-Hotels-EVEN-Hotel-Pittsburgh-Downtown.h23356627.Hotel-Information) Downtown Pittsburgh 8.8/10 Excellent (1149) "Very good breakfast and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $151 CA $172 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Pittsburgh-Hotels-EVEN-Hotel-Pittsburgh-Downtown.h23356627.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/801aa0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/aa8a56e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/bd77b326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/46a5fc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Pittsburgh [](https://www.expedia.ca/Pittsburgh-Hotels-Fairmont-Pittsburgh.h3056317.Hotel-Information) Downtown Pittsburgh 8.8/10 Excellent (1001) "Staff and location of the hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynne CA $286 CA $326 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Pittsburgh-Hotels-Fairmont-Pittsburgh.h3056317.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Emperor)](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/32e0eed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/71b0667d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/f4a5327c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kimpton Hotel Monaco Pittsburgh by IHG [](https://www.expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.Hotel-Information) Downtown Pittsburgh 9.4/10 Exceptional (1272) "This hotel is gorgeous, clean, our room was large and comfortable. My family and I plan to stay here every time we come to Pittsburgh. Also, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $234 CA $267 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.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) ![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) ![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) ### Renaissance Pittsburgh Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-Renaissance-Pittsburgh-Hotel.h581071.Hotel-Information) Downtown Pittsburgh 9.0/10 Wonderful (1004) "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 $218 CA $248 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Renaissance-Pittsburgh-Hotel.h581071.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/6b9a15fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/9ff8c760.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 (1870) "Our stay was excellent. Beautiful at Christmas! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $218 CA $249 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.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=2026-01-15&endDate=2026-01-16®ionId=6343590&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top South Side Hotel Reviews ![La Quinta Inn by Wyndham Pittsburgh Airport](https://images.trvl-media.com/lodging/1000000/10000/2500/2472/b3836cb9_y.jpg) ### La Quinta Inn by Wyndham Pittsburgh Airport 10/10 Excellent "Did not have breakfast, early flight. Easy parking, comfortable room. Pleasant staff." [](https://expedia.ca/Pittsburgh-Hotels-La-Quinta-Inn-By-Wyndham-Pittsburgh-Airport.h2472.Hotel-Information) ![Sheraton Pittsburgh Hotel at Station Square](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/ae616b8b_y.jpg) ### Sheraton Pittsburgh Hotel at Station Square 10/10 Excellent "Everything was great!" [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.Hotel-Information) ![Hyatt Regency Pittsburgh International Airport](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_y.jpg) ### Hyatt Regency Pittsburgh International Airport 10/10 Excellent "Check in took just a few minutes. Our room was very clean. Went to restaurant and bar. Lunch menu was good. " [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information) ![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 the room was very clean the pool and hot tub was an extra bonus after a busy week " [](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 "Always wonderful friendly staff. Best hotel in Pittsburgh. " [](https://expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.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 "The staff here is amazing and went above and beyond. We had a family situation and unexpectedly needed to check into the hotel on Christmas evening. Kyren at the front desk was so kind and upgraded us to a much bigger room since there were 4 of us. We enjoyed the beautiful Christmas decorations and food and drink. Thank you William Penn hotel for making our holiday bright!" [](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![Fairmont Pittsburgh](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/801aa0d0_y.jpg) ### Fairmont Pittsburgh 10/10 Excellent "I have always enjoyed Fairmont property’s. The Fairmont in Pittsburgh is in a great location. Waking distance to PNC Park, and lots of good restaurants also in walking distance. The Strip District is a very short drive as well. The hotel staff are friendly and attentive. The rooms are clean, comfortable, and modern. There is a nice bar on the second floor and the brunch on the weekend is fantastic. " [](https://expedia.ca/Pittsburgh-Hotels-Fairmont-Pittsburgh.h3056317.Hotel-Information) ![Hotel Indigo Pittsburgh East Liberty by IHG](https://images.trvl-media.com/lodging/10000000/9040000/9032700/9032700/112ecec9_y.jpg) ### Hotel Indigo Pittsburgh East Liberty by IHG 10/10 Excellent "Staff" [](https://expedia.ca/Pittsburgh-Hotels-Hotel-Indigo-Pittsburgh-East-Liberty.h9032700.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 "It’s a great stay. No issues " [](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) - [5 Star Hotels in St. Clair ](https://www.expedia.ca/5Star-St-Clair-Pittsburgh-Hotels.s50-n804081561040011264-0.Travel-Guide-Filter-Hotels) - [Hotels near Acrisure Stadium ](https://www.expedia.ca/Acrisure-Stadium-Hotels.0-l6058087-0.Travel-Guide-Filter-Hotels) - [B&B in Allegheny County ](https://www.expedia.ca/Allegheny-County-Bed-And-Breakfast.d553248635083907360-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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