A park with autumn trees, a bridge, and a building labeled UPMC in the background.

Luxury Hotels in South Side, Pittsburgh

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Luxury Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for South Side luxury hotels

A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.
A modern hotel with a prominent entrance, multiple floors, and a tall adjacent building.
A modern hotel lobby with a reception desk, a bar area, and a patterned floor.
A modern living room with a dark wood floor, a sectional sofa with decorative pillows, a round coffee table, and a fireplace.

1. The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection
Oakland
  • Rooftop terrace luxury meets university charm at this Oakland hotel with upscale dining and modern comforts.
P14,644
P16,694 total
includes taxes & fees
Oct 18 - Oct 19
The Oaklander Hotel, Autograph Collection
A spacious lobby with a high ceiling, a large cityscape mural, and a seating area with a railing.
An outdoor patio area with wicker furniture and a view of city buildings.
A spacious hotel lobby with multiple dining tables and booths, a large cityscape mural on the wall, and a high ceiling with decorative moldings.
An indoor swimming pool with clear blue water, lounge chairs, and a sunlit ceiling.

2. Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown
Downtown Pittsburgh
  • Pittsburgh sanctuary offers historical sophistication with rooftop views, indoor pool, and hot tub.
P8,010
P9,131 total
includes taxes & fees
Oct 19 - Oct 20
Drury Plaza Hotel Pittsburgh Downtown
A grand lobby with a grand piano, plush seating, chandeliers, and ornate decor.
A river with boats and a city skyline in the background.
A formal dining room with multiple tables set for service, large chandeliers, and ornate wood paneling.
A grand hallway with ornate ceiling decorations, a wooden railing, and a long corridor.

3. Omni William Penn Hotel

Omni William Penn Hotel
Downtown Pittsburgh
  • Historic elegance meets modern luxury in this Pittsburgh gem, with opulent rooms and 3 restaurants.
P14,018
P15,981 total
includes taxes & fees
Oct 29 - Oct 30
Omni William Penn Hotel
The entrance of the Hotel Monaco with a grand facade, a receptionist at the entrance, and a statue of a dog on the right.
A luxurious living room with a fireplace, plush blue sofas, a coffee table, and a chandelier.
A restaurant interior with wooden paneling, a map on the wall, and diners seated at tables.
A lobby with a yellow sofa, a chandelier, and birdcage decorations.

4. Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG
Downtown Pittsburgh
  • Indulge in downtown luxury with pillowtop beds and evening receptions at this stylish Pittsburgh retreat.
P13,822
P15,757 total
includes taxes & fees
Oct 18 - Oct 19
Kimpton Hotel Monaco Pittsburgh by IHG
A hotel with a modern facade, illuminated signage, and a covered entrance.
A hotel room with two beds, a desk, a lamp, a TV, and large windows offering city views.
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.
An outdoor patio area with multiple tables and chairs, some with potted plants.

5. DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
P9,699
P11,057 total
includes taxes & fees
Oct 25 - Oct 26
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
A rooftop lounge with seating and a view of the cityscape at dusk.
A modern hotel lobby with a reception desk, seating area, and a staircase.
A kitchen counter with various baked goods and fruits, framed artwork on the wall, and a coffee maker.
A cozy living room with a brown leather sofa, a wooden chair, and a coffee table. There is a bookshelf filled with books and decorative items.

6. Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
  • Boutique luxury in downtown Pittsburgh offers pillowtop beds, designer toiletries, and record players.
P8,173
P9,504 total
includes taxes & fees
Oct 18 - Oct 19
Joinery Hotel Pittsburgh, Curio Collection by Hilton
A hotel room with two beds, a desk, and a view of a cityscape.
A hotel room with a brown armchair, a small table with a vase of flowers, a lamp, and a view of the city through the window.
A restaurant with wooden slatted walls, leather booths, and a large window offering a view of the city.
A kitchen with wooden cabinets, a stainless steel refrigerator, a built-in microwave, and a granite countertop.

7. Fairmont Pittsburgh

Fairmont Pittsburgh
Downtown Pittsburgh
  • Indulge in Pittsburgh elegance at this downtown hotel with a full-service spa, 24-hour health club, and two distinctive restaurants.
P18,075
P20,606 total
includes taxes & fees
Oct 22 - Oct 23
Fairmont Pittsburgh
A large stone building with a central entrance, multiple windows, and a symmetrical facade.
A dark, ornate room with stained glass windows, a wooden bench, and a chandelier.
A hallway with a patterned carpet, a sofa, and framed artwork on the walls.
A dark interior with multiple stained glass windows.

8. Mansions on Fifth Hotel

Mansions on Fifth Hotel
Shadyside
  • Restored Edwardian mansion offers opulent elegance with premium beds, hydromassage showers, and designer toiletries in Shadyside.
P10,082
P11,494 total
includes taxes & fees
Oct 26 - Oct 27
Mansions on Fifth Hotel
A cityscape with high-rise buildings, including a prominent Westin hotel.
Property amenity
A coffee shop interior with shelves of coffee beans, a counter with a menu, and baskets of items on stools.
A room with large arched windows, multiple round tables with brown tablecloths, and vases with white flowers.

9. The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
P14,832
P16,908 total
includes taxes & fees
Oct 16 - Oct 17
The Westin Pittsburgh, a Marriott Hotel
A spacious lobby with a high ceiling, a central seating area, and a staircase leading to upper floors.
A modern kitchen with a bar area, seating for 8, and a large window overlooking the space.
A spacious indoor area with a high ceiling, a blue seating area, multiple tables, and a bar area.
A spacious indoor area with a modern staircase, seating areas, and a high ceiling with skylights.

10. EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG
Downtown Pittsburgh
P8,506
P9,697 total
includes taxes & fees
Oct 12 - Oct 13
EVEN Hotel Pittsburgh Downtown by IHG
View all properties

Top South Side Hotel Reviews

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

8/10 Good
"The location is great, walkable to stadiums and dining. Staff is friendly and helpful. Air conditioner was not working at first, but fixed quickly. Nearly $600 a night, as we stayed the weekend for a Steelers game, high demand time. Hotel needs some updating, but overall satisfied with stay. Breakfast and bar on site"
Michelle 2-night trip
Posted 1 hour ago
Wyndham Grand Pittsburgh Downtown
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

10/10 Excellent
"All the staff was helpful and friendly. We enjoyed our stay and will be returning again!"
Peggy Erin 2-night trip
Posted 12 hours ago
Pittsburgh Marriott City Center
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

10/10 Excellent
"Room was clean, breakfast was good but the tables were sticky."
Kelly 2-night trip
Posted 13 hours ago
Hyatt House Pittsburgh/Bloomfield/Shadyside
Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"The breakfast and happy hour were wonderful. lots of selections and it was staffed properly. The manager Kyle is definitely an asset to your organization. We will be back."
Paula 3-night trip
Posted 14 hours ago
Drury Plaza Hotel Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

8/10 Good
"Joinery overall is a great place to stay. In a great location, close to public transit. The HVAC didn’t work in the room."
Molly 2-night trip
Posted 15 hours ago
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

10/10 Excellent
"Super awesome rooms"
Jodel 1-night trip
Posted 21 hours ago
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

10/10 Excellent
"Staff was great"
Michael 3-night trip
Posted 2 days ago
Courtyard by Marriott Pittsburgh University Center
Springhill Suites by Marriott Pittsburgh North Shore

Springhill Suites by Marriott Pittsburgh North Shore

10/10 Excellent
"The hotel was clean, comfortable and had a perfect location for a Steelers game and enjoying the North Shore area!"
Jennifer 3-night trip
Posted 2 days ago
Springhill Suites by Marriott Pittsburgh North Shore

Explore a world of travel with Expedia