Title: Book the Best ROMANTIC Hotels in South Side, PA from CA $99 - South Side Romantic Getaways | 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 Romantic Hotels in South Side, PA from CA $99 - ![](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 Romantic Hotels Tonight [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This 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&travelerType=romantic) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for South Side romantic hotels ![Living area](https://images.trvl-media.com/lodging/84000000/83320000/83313300/83313227/38d99c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Queen Beds, City View](https://images.trvl-media.com/lodging/84000000/83320000/83313300/83313227/e98077b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, Multiple Beds, Ensuite, Corner | Living area](https://images.trvl-media.com/lodging/84000000/83320000/83313300/83313227/f6947031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, Multiple Beds, Ensuite, Corner](https://images.trvl-media.com/lodging/84000000/83320000/83313300/83313227/5f5bd81d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Traveler's Rest Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-Travelers-Rest-Hotel.h83313227.Hotel-Information) South Side Flats 9.6/10 Exceptional (92) "This might be the coolest place I have ever stayed. Rooms are small (used to be a hostel) but spotless as is the rest of the hotel. Great history behind this building. Very comfortable sitting in the great room conversing with others. The peacefulness was in large part due to this being a TV free hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) craig [](https://www.expedia.ca/Pittsburgh-Hotels-Travelers-Rest-Hotel.h83313227.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/34000000/33230000/33229300/33229225/9b751878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/34000000/33230000/33229300/33229225/dde48ad1.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/34000000/33230000/33229300/33229225/w2080h1566x0y14-75158592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33230000/33229300/33229225/88d390c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRYP by Wyndham Pittsburgh/Lawrenceville [](https://www.expedia.ca/Pittsburgh-Hotels-TRYP-By-Wyndham-PittsburghLawrenceville.h33229225.Hotel-Information) Lawrenceville 8.6/10 Excellent (1005) "Room was nice and clean. Staff very friendly, especially the valet workers. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassie CA $86 CA $99 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-TRYP-By-Wyndham-PittsburghLawrenceville.h33229225.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/b7421ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/bb1304d8.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/1000000/30000/20400/20319/d3e2da96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/afc4eef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Pittsburgh Hotel at Station Square [](https://www.expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.Hotel-Information) South Shore 9.0/10 Wonderful (1001) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gail CA $183 CA $209 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.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) ![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) ![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) ![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 (3299) "Very nice place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CAROLYN CA $174 CA $198 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/43500/43447/aaf723c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/1000000/50000/43500/43447/f542d276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/43500/43447/d21cf974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/43500/43447/f4f64a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pittsburgh Marriott City Center [](https://www.expedia.ca/Pittsburgh-Hotels-Marriott-Pittsburgh-City-Center-Hotel.h43447.Hotel-Information) Downtown Pittsburgh 8.0/10 Very good (1073) "Friendly and helpful staff, great breakfast and comfortable rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $152 CA $173 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Pittsburgh-Hotels-Marriott-Pittsburgh-City-Center-Hotel.h43447.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/24000000/23360000/23356700/23356627/0a830eb6.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/24000000/23360000/23356700/23356627/0579f884.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) ![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 (1152) "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) ![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 (1857) "Everything about our stay at the William Penn was was wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $212 CA $242 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1103000/1102934/0a02879e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1110000/1103000/1102934/96947cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1103000/1102934/0a89d988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1110000/1103000/1102934/2a96afdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Priory Hotel [](https://www.expedia.ca/Pittsburgh-Hotels-The-Priory-Hotel.h1102934.Hotel-Information) North Side 9.4/10 Exceptional (1000) "Would have liked more traditional sit down breakfast but overall, a very lovely place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $151 CA $173 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Pittsburgh-Hotels-The-Priory-Hotel.h1102934.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/8b478daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/8d96d2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/96a735d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/d21b758d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Pittsburgh University Center [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Pittsburgh-University-Center.h3215.Hotel-Information) Oakland 9.0/10 Wonderful (558) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $167 CA $190 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Pittsburgh-University-Center.h3215.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/9f3454ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/bd0bb9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/w3839h2559x0y0-3c3f5e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/0596396e.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 (1047) "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) 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=2026-01-08&endDate=2026-01-09®ionId=6343590&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![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) ![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) ![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg) ### The Westin Pittsburgh, a Marriott Hotel 10/10 Excellent "The hotel was beautiful, clean and the staff was super friendly. " [](https://expedia.ca/Pittsburgh-Hotels-The-Westin-Pittsburgh.h14295.Hotel-Information) ![Pittsburgh Marriott City Center](https://images.trvl-media.com/lodging/1000000/50000/43500/43447/aaf723c4_y.jpg) ### Pittsburgh Marriott City Center 10/10 Excellent "Location and restaurant " [](https://expedia.ca/Pittsburgh-Hotels-Marriott-Pittsburgh-City-Center-Hotel.h43447.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 "Clean and friendly staff" [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.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 "The room was clean, the staff was very nice and helpful. The complementary breakfast was one of the best that I have had in a hotel " [](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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