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 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-26&endDate=2025-12-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-27&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next 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) ## 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) ![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) ![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) ![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 $165 CA $278 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Kasa-Pittsburgh-South-Side.h70891071.Hotel-Information) ![Premium Room](https://images.trvl-media.com/lodging/37000000/36050000/36047400/36047368/6e14794a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Courtyard View](https://images.trvl-media.com/lodging/37000000/36050000/36047400/36047368/ecadac1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Courtyard View](https://images.trvl-media.com/lodging/37000000/36050000/36047400/36047368/61c1f6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/37000000/36050000/36047400/36047368/1a9bf6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villagio Boutique Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-The-Parador-Inn.h36047368.Hotel-Information) North Side 9.6/10 Exceptional (72) "Large comfortable room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tony CA $142 CA $162 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Parador-Inn.h36047368.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/95000000/94960000/94951900/94951877/6a2868cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/95000000/94960000/94951900/94951877/03bcd480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/95000000/94960000/94951900/94951877/99ba8614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94960000/94951900/94951877/fa5c4073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hickory House Bed & Breakfast [](https://www.expedia.ca/Hickory-Hotels-Hickory-House-Bed-Breakfast.h94951877.Hotel-Information) Hickory 10/10 Exceptional (32) "Hosts were the most friendly people I’ve ever met! 10/10 will go back every time for concerts at the star lake pavilion " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan [](https://www.expedia.ca/Hickory-Hotels-Hickory-House-Bed-Breakfast.h94951877.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/07abcae9.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) ![Indoor wedding](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/aa8a56e9.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 (1002) "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 Dec 27 - Dec 28 [](https://www.expedia.ca/Pittsburgh-Hotels-Fairmont-Pittsburgh.h3056317.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) ![Interior entrance](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/98e3a2c0.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) ![Terrace/patio](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/w4000h2665x0y2-dfe4b7a7.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) ### The Oaklander Hotel, Autograph Collection [](https://www.expedia.ca/Pittsburgh-Hotels-The-Oaklander-Hotel.h28852483.Hotel-Information) Oakland 9.2/10 Wonderful (727) "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 $286 CA $326 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Oaklander-Hotel.h28852483.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) ![Interior](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/f4a5327c.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) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/6d4ea109.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 (1267) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $234 CA $267 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/cd0b7628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/eec6027c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/f76e4b47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown [](https://www.expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.Hotel-Information) Downtown Pittsburgh 8.2/10 Very good (1045) "Staff friendly, rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard Daryl CA $163 CA $186 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/4e887670.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 (1413) "Room was clean and staff was nice. Location was great! A little pricey though paying for breakfast and parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raneisha CA $156 CA $181 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.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 (1150) "Very good breakfast and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $148 CA $168 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Pittsburgh-Hotels-EVEN-Hotel-Pittsburgh-Downtown.h23356627.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=2026-01-09&endDate=2026-01-10®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 "The staff were friendly and so very helpful. The room was very clean and the location is great when needing to get to the airport early. Appreciated the shuttle service and the help of the employees to figure out the best time of departure. Would definitely stay again " [](https://expedia.ca/Pittsburgh-Hotels-La-Quinta-Inn-By-Wyndham-Pittsburgh-Airport.h2472.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 "Watched a football game at the bar and stayed overnight for a 6am flight. Our bartender was friendly and funny. Food was excellent and the bed and pillows were extremely comfortable. A great stay before our holiday cruise." [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information) ![DoubleTree by Hilton Pittsburgh - Green Tree](https://images.trvl-media.com/lodging/1000000/20000/12400/12343/ea79878f_y.jpg) ### DoubleTree by Hilton Pittsburgh - Green Tree 10/10 Excellent "Great place and awesome breakfast!" [](https://expedia.ca/Pittsburgh-Hotels-Doubletree-By-Hilton-Pittsburgh-Greentree.h12343.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 "This is probably the best place to stay in Pittsburgh, for the view." [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.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 "Everything was great!" [](https://expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.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 "Great place close to everything." [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.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 "Great downtown location. Good kickback and breakfast options. " [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.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 "Everything about our stay at the William Penn was was wonderful. " [](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.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 "Everything was top notch" [](https://expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.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) - 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