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

Find Romantic Hotels in South Side, PA

  • 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 Romantic Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for South Side romantic hotels

A modern dining area with a round table, chairs, and a sofa. There are large windows providing natural light and a view of the outdoors.
A hotel room with a bed, desk, chair, and a small table with a tray.
A multi-story hotel with a brick facade and a flat roof.
A well-organized snack and beverage area with shelves stocked with various snacks and a refrigerated section labeled 'market'.

1. SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works
South Side Flats
United States
Angel Leonel
₩165,780
₩188,990 total
includes taxes & fees
Oct 12 - Oct 13
SpringHill Suites by Marriott Pittsburgh Southside Works
An outdoor seating area with wicker furniture and a view of a river and buildings in the background.
A modern indoor swimming pool with clear glass walls, a blue-tiled edge, and a view of trees and buildings outside.
A multi-story hotel with a prominent 'Hyatt House' sign, featuring a modern architectural design with a flat roof and large windows.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

2. HYATT house Pittsburgh-South Side

HYATT house Pittsburgh-South Side
South Side Flats
United States
Jonathan
₩173,478
₩197,765 total
includes taxes & fees
Oct 19 - Oct 20
HYATT house Pittsburgh-South Side
A spacious indoor area with multiple tables and chairs, a brick wall, and hanging star-shaped lights.
A multi-story hotel with a modern design, featuring a prominent entrance and a visible sign for the hotel.
A modern lobby with a reception desk, seating area, and a large window with a view.
An outdoor seating area with a stone fireplace, red chairs, and a metal table.

3. Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place
Oakland
United States
Betsey
₩181,610
₩207,036 total
includes taxes & fees
Oct 21 - Oct 22
Residence Inn Pittsburgh Oakland/University Place
A breakfast bar with various food items and a sign that says "Egg-Xactly The Start You Need".
An indoor swimming pool with clear glass walls, a blue chair, and a small round table in the center.
A modern dining area with high tables and chairs, large windows, and artwork on the walls.
A hotel room with two beds, a desk, and a chair.

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

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
South Side Flats
United States
Dianne
₩117,911
₩134,418 total
includes taxes & fees
Oct 21 - Oct 22
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
A Marriott hotel with a modern glass facade, surrounded by other buildings and a historic building in the background.
A hotel dining area with multiple tables and chairs, large windows with city views, and a patterned carpet.
A bar area with a long counter, multiple shelves of liquor bottles, and bar stools.
A hotel reception area with a modern design, featuring a reception desk with illuminated panels, a seating area with a bench and chairs, and a large wall with a geometric art piece.

5. Pittsburgh Marriott City Center

Pittsburgh Marriott City Center
Downtown Pittsburgh
United States
eric
₩206,209
₩235,078 total
includes taxes & fees
Oct 18 - Oct 19
Pittsburgh Marriott City Center
A spacious living room with a wooden ceiling, large windows with curtains, a leather sofa, a dining table, and a kitchen area.
A room with wooden paneling, a fireplace, a mirror, and a wardrobe.
A room with a bed, a chair, a table, a lamp, and a fireplace.
A brick building with a wooden door labeled "Southside Traveler's Rest."

6. Traveler's Rest Hotel

Traveler's Rest Hotel
South Side Flats
United States
Amber
₩145,995
₩166,435 total
includes taxes & fees
Oct 21 - Oct 22
Traveler's Rest Hotel
A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.
A modern kitchen area with a buffet setup, including a counter with food containers and a chalkboard menu.
A swimming pool with chairs and a view of a red brick building.
A compact kitchen with a built-in microwave, dishwasher, and a sink. There's a gray sofa in the adjacent living area, and a large framed artwork on the wall.

7. Hampton Inn & Suites Pittsburgh-Downtown

Hampton Inn & Suites Pittsburgh-Downtown
Downtown Pittsburgh
United States
Michael
₩187,817
₩214,111 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn & Suites Pittsburgh-Downtown
An outdoor seating area with a stone fire pit, cushioned sofas, and a table with chairs.
A modern kitchen with a central island, built-in shelves, and a large window.
A modern kitchen with a central island, bar stools, a flat-screen TV, and a seating area with a sofa and a lamp.
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, and large windows offering views of the outside.

8. Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside
Bloomfield
United States
David
₩206,006
₩234,847 total
includes taxes & fees
Oct 19 - Oct 20
Hyatt House Pittsburgh/Bloomfield/Shadyside
A spacious lobby with modern furniture, large windows, and an exit sign.
A modern hotel lobby with round tables, yellow chairs, a bar area, and a kitchen in the background.
A modern hotel lobby with a reception desk, seating area, and a view of the cityscape.
A corner market with refrigerated beverage dispensers and snack shelves.

9. Fairfield Inn & Suites by Marriott Pittsburgh Downtown

Fairfield Inn & Suites by Marriott Pittsburgh Downtown
Downtown Pittsburgh
United States
Alex Michael
₩204,304
₩232,906 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield Inn & Suites by Marriott Pittsburgh Downtown
A modern living room with a fireplace, sofas, and a large window overlooking a cityscape at night.
A bar area with a marble countertop, wooden bar stools, and a television mounted on the wall.
An outdoor seating area with wicker furniture, a fire feature, and a modern building in the background.
A hotel lobby with a reception desk, seating area, and a large chandelier.

10. Homewood Suites by Hilton Pittsburgh Downtown

Homewood Suites by Hilton Pittsburgh Downtown
Downtown Pittsburgh
United States
Junhong
₩224,169
₩255,553 total
includes taxes & fees
Oct 18 - Oct 19
Homewood Suites by Hilton Pittsburgh Downtown
View all properties

Top South Side Hotel Reviews

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"Older hotel but well kept up and in a prime location! Great buffet, nice indoor pool and outdoor patio. Only thing lacking was the micro sized fitness center. This location is walkable to several museums, the Strip, PNC ball park….."
Susan 3-night trip
Posted 6 hours ago
Drury Plaza Hotel Pittsburgh Downtown
Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

8/10 Good
"Pretty decent price. Clean, spacious room. Disappointed that I booked a shower/tub combo room but was given a walk in shower. I enjoy winding down in a hot bath at night. I always check the listing to ensure I book the tub. Put a damper on my stay. Also took off a star for breakfast. Pictures on their advertising sites show BACON. They do NOT have bacon. Just the cheap sausage patties it seems everyone reverted to since Covid. Coffee was good quality. Freshly ground beans. Overall it was a decent hotel, but you don’t get what is actually advertised."
Marlow 1-night trip
Posted 8 hours ago
Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

8/10 Good
"one night stay, one great experience"
Marcos 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Pittsburgh - Green Tree
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

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

10/10 Excellent
"We had a very enjoyable stay! Everyone was polite, professional. Special thanks to Ebony who went out of her way to assist us when needed and went above and beyond to make sure we had a great experience at the hotel!"
Richard 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Explore a world of travel with Expedia