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Our top choices for South Side hotels with a casino

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHGSouth Side Flats
7.2 out of 10, Good, (1003)
The price is ¥12,931
¥14,740 total
includes taxes & fees
Dec 25 - Dec 26

4 Bedroom Beauty Spacious Home in Southside
4 Bedroom Beauty Spacious Home in SouthsideSouth Side Flats
The price is ¥16,670
¥41,587 total
includes taxes & fees
Dec 12 - Dec 13

King Bed | Free Parking | Arcade | Fire Pit
King Bed | Free Parking | Arcade | Fire PitSouth Side Flats
10.0 out of 10, Exceptional, (23)
The price is ¥20,253
¥56,798 total
includes taxes & fees
Jan 6 - Jan 7, 2026

The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!South Side Flats
8.0 out of 10, Very Good, (1)

Hot Tub | King Bed | Games | Free Parking
Hot Tub | King Bed | Games | Free ParkingSouth Side Flats
10.0 out of 10, Exceptional, (4)
The price is ¥21,811
¥58,749 total
includes taxes & fees
Dec 17 - Dec 18

Fun Crash Pad • City Views • Off-Street Parking
Fun Crash Pad • City Views • Off-Street ParkingSouth Side Slopes
7.8 out of 10, Good, (12)
The price is ¥25,394
¥46,580 total
includes taxes & fees
Jan 3 - Jan 4, 2026

Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking SpacesSouth Side Flats
10.0 out of 10, Exceptional, (20)
The price is ¥52,345
¥96,649 total
includes taxes & fees
Dec 11 - Dec 12

King Bed | Free Parking | BBQ | Fire pit | Arcade
King Bed | Free Parking | BBQ | Fire pit | ArcadeSouth Side Flats
9.8 out of 10, Exceptional, (66)
The price is ¥16,046
¥53,207 total
includes taxes & fees
Dec 17 - Dec 18
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.
Top South Side Hotel Reviews

Kimpton Hotel Monaco Pittsburgh by IHG
10/10 Excellent
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