Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Traveler's Rest Hotel
Price was $462, price is now $377 per person
$377
per person
Sep 16 - Sep 18
found 16 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free bicycles on site. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Lovely place. Easy to park on the street, and easy access to downtown Pittsburgh (we were in town for a concert). Private and secure bathroom is just down the hall from the Family Room. The room itself was nice and the common area was very cozy. Breakfast was good with lot of options. Would definitely stay again!
Reviewed on Jun 18, 2026
Stay Pittsburgh
Price was $611, price is now $427 per person
$427
per person
Sep 16 - Sep 18
found 16 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this aparthotel in Pittsburgh. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Only one towel and one washcloth for a two night stay. AC is evident, but rooms have no control of it. Bed was lumpy, hard and uncomfortable.
Reviewed on Jun 25, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Price was $846, price is now $639 per person
$639
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
This hotel was great! The staff was fantastic. The restaurant was nice. Everything was great!
Reviewed on Jun 29, 2026
The Westin Pittsburgh, a Marriott Hotel
Price was $1,136, price is now $921 per person
$921
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Wichita (ICT) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions PPG Paints Arena and PNC Park are located nearby.
It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.
Reviewed on Jun 24, 2026
Homewood Suites by Hilton Pittsburgh Southpointe
Price was $852, price is now $691 per person
$691
per person
Aug 10 - Aug 16
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Canonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hollywood Casino at the Meadows and Southpointe Town Center are located nearby.
Had a 5 day stay and no cleaning of the room, they did compensate for the misstep.
Reviewed on Jun 29, 2026
SpringHill Suites by Marriott Pittsburgh Bakery Square
Price was $1,365, price is now $1,121 per person
$1,121
per person
Aug 10 - Aug 16
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Spacious rooms. Beautiful location.
Reviewed on Jun 19, 2026
Pittsburgh Marriott City Center
Price was $733, price is now $606 per person
$606
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Staff was amazing and welcoming!
Room were very large and roomie with great city views.
Location was spot on.
Front desk one of the best service staff !
Virginia
Reviewed on Jun 30, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Price was $907, price is now $751 per person
$751
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Wichita (ICT) to Pittsburgh (PIT)
Stay at this apartment in Pittsburgh. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions PPG Paints Arena and PNC Park are located nearby.
Room was clean, staff was friendly, check in/out was easy, I would definitely recommend.
Reviewed on Jun 29, 2026
South Side Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Side Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Aug 26 - Sat, Aug 29
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Wed, Aug 19 - Sat, Aug 22
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Wed, Aug 19 - Sat, Aug 29
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$193 Roundtrip, found 19 hours ago
$193
Roundtrip
found 19 hours ago
Tue, Aug 18 - Tue, Sep 1
DEN
Denver Intl.
PIT
Pittsburgh Intl.
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
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