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

Best Luxury Hotels in South Side

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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 living room with a dark wood floor, a sectional sofa with decorative pillows, a round coffee table, and a fireplace.
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.

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.
RM955
RM1,089 total
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.
An indoor swimming pool with clear blue water, lounge chairs, and a sunlit ceiling.
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.
RM522
RM596 total
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 spacious lobby with a red carpet, ornate ceiling, and a staircase leading to upper floors.
A formal dining room with multiple tables set for service, large chandeliers, and ornate wood paneling.
A river with boats and a city skyline in the background.

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.
RM914
RM1,042 total
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 restaurant interior with wooden paneling, a map on the wall, and diners seated at tables.
A luxurious living room with a fireplace, plush blue sofas, a coffee table, and a chandelier.

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.
RM902
RM1,029 total
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.
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
RM633
RM721 total
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 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.
A kitchen counter with various baked goods and fruits, framed artwork on the wall, and a coffee maker.
A spacious lobby with a grand staircase, seating areas, and a mezzanine level.

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.
RM533
RM620 total
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 kitchen with wooden cabinets, a stainless steel refrigerator, a built-in microwave, and a granite countertop.
A restaurant with wooden slatted walls, leather booths, and a large window offering a view of the city.
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.
RM1,180
RM1,345 total
includes taxes & fees
16 Oct - 17 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.
RM658
RM750 total
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.
Property amenity
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
RM968
RM1,103 total
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 modern staircase, seating areas, and a high ceiling with skylights.
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.

10. EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG
Downtown Pittsburgh
RM555
RM633 total
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 4 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 5 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 7 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
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

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