Find Romantic Hotels in South Side, PA

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for South Side romantic hotels

An outdoor seating area with wicker furniture and a view of a river and buildings in the background.

1. HYATT house Pittsburgh-South Side

HYATT house Pittsburgh-South Side
3.0 star property
South Side Flats
8.8 out of 10, Excellent, (1,002 reviews)
"Great location, spacious room, nice view, friendly staff."
United States
Adrienne
The price is £115
includes taxes & fees
11 Nov - 12 Nov
HYATT house Pittsburgh-South Side
An outdoor deck with a fire feature, seating, and a view of the city at night.

2. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay in this beautiful home! The host was super responsive and helpful. The home is spacious and well kept with amazing views of the city. The cherry on top was the driveway/parking area that accommodated our five vehicles. Great choice for our family get together!"
United States
Mary H.
The price is £316
includes taxes & fees
9 Nov - 10 Nov
City Skyline - Outside decks - Contemporary
A grand lobby with a grand piano, plush seating, chandeliers, and ornate decor.

3. Omni William Penn Hotel

Omni William Penn Hotel
4.0 star property
Downtown Pittsburgh
9.2 out of 10, Wonderful, (2,020 reviews)
"Beautiful hotel, very clean and would definitely stay again!"
United States
Lori
The price is £122
includes taxes & fees
29 Nov - 30 Nov
Omni William Penn Hotel
A spacious lobby with a high ceiling, a large cityscape mural, and a seating area with a railing.

4. Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown
4.0 star property
Downtown Pittsburgh
9.4 out of 10, Exceptional, (2,433 reviews)
"All around great place to stay."
United States
Stephen
The price is £95
includes taxes & fees
16 Nov - 17 Nov
Drury Plaza Hotel Pittsburgh Downtown
A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.

5. The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection
4.5 star property
Oakland
9.2 out of 10, Wonderful, (853 reviews)
"Great location, upscale amenities and really tasty food."
United States
William
The price is £155
includes taxes & fees
23 Nov - 24 Nov
The Oaklander Hotel, Autograph Collection
A hotel room with a large mirror, a bedside table with toiletries, two beds, a wardrobe, and a view of the outside through two windows.

6. TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville
3.0 star property
Lawrenceville
8.6 out of 10, Excellent, (1,236 reviews)
"Great place to stay! Amazing location to so many restaurants and bars and shops. Super clean and great rooms with great views of the city!"
United States
Alayna
The price is £68
includes taxes & fees
22 Nov - 23 Nov
TRYP by Wyndham Pittsburgh/Lawrenceville
A Marriott hotel with a modern glass facade, surrounded by other buildings and a historic building in the background.

7. Pittsburgh Marriott City Center

Pittsburgh Marriott City Center
3.5 star property
Downtown Pittsburgh
8.2 out of 10, Very good, (1,390 reviews)
"Comfy beds, good breakfast, will definitely stay again!"
United States
Jennifer
The price is £115
includes taxes & fees
22 Nov - 23 Nov
Pittsburgh Marriott City Center
A double door with a stone frame and a decorative arch above it.

8. The Maverick by Kasa

The Maverick by Kasa
3.0 star property
East Liberty
9.0 out of 10, Wonderful, (1,016 reviews)
"Lovely place, convenient for going places and reasonable prices."
United States
Yanbei
The price is £73
includes taxes & fees
29 Nov - 30 Nov
The Maverick by Kasa
A Courtyard by Marriott hotel with a covered entrance, brick facade, and a parking lot with handicapped accessibility.

9. Courtyard by Marriott Pittsburgh West Homestead/Waterfront

Courtyard by Marriott Pittsburgh West Homestead/Waterfront
3.0 star property
West Homestead
8.2 out of 10, Very good, (1,001 reviews)
"Very clean and well maintained! Thank You so much!❤️"
United States
Leila
The price is £107
includes taxes & fees
22 Nov - 23 Nov
Courtyard by Marriott Pittsburgh West Homestead/Waterfront
A rooftop lounge with seating and a view of the cityscape at dusk.

10. Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton
4.0 star property
Downtown Pittsburgh
8.4 out of 10, Very good, (1,710 reviews)
"Great location."
United States
Eric
The price is £119
includes taxes & fees
22 Nov - 23 Nov
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

A grand lobby with a grand piano, plush seating, chandeliers, and ornate decor.
Omni William Penn Hotel

Omni William Penn Hotel

Omni William Penn Hotel
Downtown Pittsburgh

10/10 Excellent

A great traditional style hotel in superb location.
United Kingdom
Dale
Reviewed September 17, 2026
Omni William Penn Hotel

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