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

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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 hotel lobby with a reception desk, a bar area, and a patterned floor.
A modern hotel with a prominent entrance, multiple floors, and a tall adjacent building.
A modern rooftop lounge with large windows, blue seating, and a city view.

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.
S$328
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 hotel room with a large bed, a television, two framed pictures on the wall, and a patterned carpet.
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 outdoor patio area with wicker furniture and a view of city buildings.

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.
S$192
includes taxes & fees
22 Oct - 23 Oct
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 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.

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.
S$326
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 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.
A restaurant interior with wooden paneling, a map on the wall, and diners seated at tables.

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.
S$322
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.
An outdoor patio area with multiple tables and chairs, some with potted plants.
A modern hotel lobby with a reception desk, seating area with sofas and chairs, and a large window providing natural light.
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

5. DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
S$221
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 modern hotel lobby with a reception desk, seating area, and a staircase.
A spacious lobby with a grand staircase, seating areas, and a mezzanine level.
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 city centre Pittsburgh offers pillowtop beds, designer toiletries, and record players.
S$186
includes taxes & fees
25 Oct - 26 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 kitchen with wooden cabinets, a stainless steel refrigerator, a built-in microwave, and a granite countertop.
A spacious hall with rows of chairs, a central aisle, and a decorative backdrop.

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.
S$421
includes taxes & fees
1 Oct - 2 Oct
Fairmont Pittsburgh
A large stone building with a central entrance, multiple windows, and a symmetrical facade.
A dark interior with multiple stained glass windows.
A dark, ornate room with stained glass windows, a wooden bench, and a chandelier.
A spacious living room with high ceilings and wooden paneling, featuring two armchairs, a coffee table, and a fireplace.

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.
S$235
includes taxes & fees
26 Oct - 27 Oct
Mansions on Fifth Hotel
A cityscape with high-rise buildings, including a prominent Westin hotel.
A modern hotel lobby with a sectional sofa, ottomans, armchairs, a wooden bookshelf, and a patterned carpet.
A room with large arched windows, multiple round tables with brown tablecloths, and vases with white flowers.
A coffee shop interior with shelves of coffee beans, a counter with a menu, and baskets of items on stools.

9. The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
S$345
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 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.
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
S$198
includes taxes & fees
12 Oct - 13 Oct
EVEN Hotel Pittsburgh Downtown by IHG
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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 4 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 6 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 12 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
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 1 day ago
Springhill Suites by Marriott Pittsburgh North Shore

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