Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Price was $555, price is now $483 per person
$483
per person
Nov 19 - Nov 21
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Westin Pittsburgh, a Marriott Hotel
Price was $1,041, price is now $842 per person
$842
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Traveler's Rest Hotel
Price was $1,108, price is now $942 per person
$942
per person
Dec 18 - Dec 21
found 2 hours ago
Roundtrip flight included
New York (NYC) 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.
Very unique building. Very nice hosts.
Reviewed on Oct 7, 2026
DoubleTree by Hilton Pittsburgh - Green Tree
Price was $767, price is now $653 per person
$653
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Acrisure Stadium and PNC Park are located nearby.
DoubleTree by Hilton Pittsburgh - Cranberry
Price was $634, price is now $543 per person
$543
per person
Dec 18 - Dec 21
found 2 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Mars. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions UPMC Lemieux Sports Complex and Seven Fields Nature Preserve are located nearby.
Hyatt Regency Pittsburgh International Airport
Price was $828, price is now $716 per person
$716
per person
Dec 23 - Dec 27
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 a free airport shuttle. Our guests praise the restaurant and the bar in our reviews. Popular attractions The Mall at Robinson and Joe Walton Stadium are located nearby.
Matt the bartender always is welcoming & is excellent at his service
Reviewed on Oct 8, 2026
The Maverick by Kasa
Price was $618, price is now $535 per person
$535
per person
Dec 18 - Dec 21
found 2 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free WiFi, a 24-hour business center, and cable TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Fairmont Pittsburgh
Price was $761, price is now $663 per person
$663
per person
Nov 19 - Nov 21
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this luxury hotel in Pittsburgh. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and PPG Paints Arena are located nearby.
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.
Tue, Nov 10 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$170 Roundtrip, found 20 hours ago
$170
Roundtrip
found 20 hours ago
Wed, Oct 28 - Sat, Oct 31
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$228 Roundtrip, found 20 hours ago
$228
Roundtrip
found 20 hours ago
Wed, Nov 4 - Thu, Nov 19
DFW
Dallas-Fort Worth Intl.
PIT
Pittsburgh Intl.
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Sat, Nov 14 - Tue, Nov 17
DAL
Love Field
PIT
Pittsburgh Intl.
$241 Roundtrip, found 20 hours ago
$241
Roundtrip
found 20 hours ago
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