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

South Side Hotel Guide - 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
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 rooftop lounge with large windows, blue seating, and a city view.
A modern hotel with a prominent entrance, multiple floors, and a tall adjacent building.
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.
€235
includes taxes & fees
18 Oct - 19 Oct
The Oaklander Hotel, Autograph Collection
A spacious lobby with a high ceiling, a large cityscape mural, and a seating area with a railing.
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.
A hotel room with a large bed, a television, two framed pictures on the wall, and a patterned carpet.

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.
€129
includes taxes & fees
19 Oct - 20 Oct
Drury Plaza Hotel Pittsburgh Downtown
A grand lobby with a grand piano, plush seating, chandeliers, and ornate decor.
A grand hallway with ornate ceiling decorations, a wooden railing, and a long corridor.
A formal dining room with multiple tables set for service, large chandeliers, and ornate wood paneling.
A spacious lobby with a red carpet, ornate ceiling, and a staircase leading to upper floors.

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.
€225
includes taxes & fees
29 Oct - 30 Oct
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 lobby with a yellow sofa, a chandelier, and birdcage decorations.
A luxurious living room with a fireplace, plush blue sofas, a coffee table, and a chandelier.
A rooftop terrace with round tables and chairs, string lights, and a city view.

4. Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG
Downtown Pittsburgh
  • Indulge in city centre luxury with pillowtop beds and evening receptions at this stylish Pittsburgh retreat.
€222
includes taxes & fees
18 Oct - 19 Oct
Kimpton Hotel Monaco Pittsburgh by IHG
A hotel with a modern facade, illuminated signage, and a covered entrance.
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.
A modern hotel lobby with a reception desk, seating area with sofas and chairs, and a large window providing natural light.
A hotel room with two beds, a desk, a lamp, a TV, and large windows offering city views.

5. DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
€156
includes taxes & fees
25 Oct - 26 Oct
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
A rooftop lounge with seating and a view of the cityscape at dusk.
A spacious lobby with a grand staircase, seating areas, and a mezzanine level.
A kitchen counter with various baked goods and fruits, framed artwork on the wall, and a coffee maker.
A modern hotel lobby with a reception desk, seating area, and a staircase.

6. Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
  • Boutique luxury in city centre Pittsburgh offers pillowtop beds, designer toiletries, and record players.
€138
includes taxes & fees
18 Oct - 19 Oct
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 spacious hall with rows of chairs, a central aisle, and a decorative backdrop.
A restaurant with wooden slatted walls, leather booths, and a large window offering a view of the city.

7. Fairmont Pittsburgh

Fairmont Pittsburgh
Downtown Pittsburgh
  • Indulge in Pittsburgh elegance at this city centre hotel with a full-service spa, 24-hour health club, and two distinctive restaurants.
€290
includes taxes & fees
1 Oct - 2 Oct
Fairmont Pittsburgh
A large stone building with a central entrance, multiple windows, and a symmetrical facade.
A hallway with a patterned carpet, a sofa, and framed artwork on the walls.
A spacious living room with high ceilings and wooden paneling, featuring two armchairs, a coffee table, and a fireplace.
A dark, ornate room with stained glass windows, a wooden bench, and a chandelier.

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.
€162
includes taxes & fees
26 Oct - 27 Oct
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
€238
includes taxes & fees
16 Oct - 17 Oct
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 spacious indoor area with a high ceiling, a blue seating area, multiple tables, and a bar area.
A spacious indoor area with a high ceiling, a mezzanine level, and a central open space with seating and tables.
A modern kitchen with a bar area, seating for 8, and a large window overlooking the space.

10. EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG
Downtown Pittsburgh
€137
includes taxes & fees
12 Oct - 13 Oct
EVEN Hotel Pittsburgh Downtown by IHG
View all properties

Top South Side Hotel Reviews

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 3 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 4 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 5 hours ago
Drury Plaza Hotel Pittsburgh Downtown
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

8/10 Good
"There's no microwave in the room. Can't warm any food in the room"
LYNN 2-night trip
Posted 6 hours ago
Wyndham Grand 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 7 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 13 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 1 day ago
Courtyard by Marriott Pittsburgh University Center

Explore a world of travel with Expedia