Deals on vacations and trips to South Side

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South Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn on Negley

The Inn on Negley

4 out of 5
Shadyside
Price was $662, price is now $578 per person
$578
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
This inn doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, a garden, and a computer station are also on offer.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $1,087, price is now $826 per person
$826
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Free WiFi in public areas, express check-in, and express check-out are available at this aparthotel. Luggage storage, laundry facilities, and a virtual front desk are also on offer.
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was $1,230, price is now $1,036 per person
$1,036
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
Free WiFi in public areas, a garden, and express check-in are available at this vacation home. A free airport shuttle is offered as well. Express check-out, a computer station, and luggage storage are also on offer.
Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $743, price is now $649 per person
$649
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Free WiFi in public areas, a communal living room, and express check-in are available at this hotel. Enjoy the free self-serve breakfast each morning. Express check-out, luggage storage, and laundry facilities are also on offer.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $859, price is now $751 per person
$751
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and express check-out are also provided.

Top South Side hotels deals

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

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

2.5 out of 5
20 S 10th St Pittsburgh PA
Free Cancellation
The price is $106 total per night
$106 total
per night
Oct 20 - Oct 21
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free buffet breakfast is served.
Pool
Breakfast included
SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
2950 S Water St Pittsburgh PA
The price is $139 total per night
$139 total
per night
Oct 4 - Oct 5
This hotel doesn't skimp on freebies - guests receive free breakfast and free WiFi. Traveling on business? Take advantage of the express check-out and free internet in public areas. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Free WiFi
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
The price is $141 total per night
$141 total
per night
Oct 12 - Oct 13
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and express check-out are also provided.
Pool
Pet friendly
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
The price is $173 total per night
$173 total
per night
Oct 16 - Oct 17
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a grocery/convenience store, and a lobby fireplace are also offered.
Pet friendly
Free WiFi
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
The price is $155 total per night
$155 total
per night
Oct 28 - Oct 29
A casino, 5 restaurants, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and free valet parking. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like continental breakfast and free self parking.
Breakfast included
Parking included
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
The price is $136 total per night
$136 total
per night
Oct 27 - Oct 28
This hotel features a restaurant, a gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, a 24-hour business center, and a coffee shop are also offered.
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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.

Stay near popular South Side attractions

Rex Theater

6.0/10 (1 review)
You can get tickets for a performance at Rex Theater on your trip to Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
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Frequently asked questions

How much are vacation packages to South Side?
Travelocity provides package deals to South Side, as well as flights and hotels, from an impressive $578. With the money you save, you could book some cool tours or possibly tack on a few extra nights to your exciting getaway.
Where can I get the best vacation package deals for South Side?
For a fun and affordable package deal to South Side, turn to Travelocity. Select from 400 airlines and 1,000,000 properties around the world to create the ideal adventure — you're spoiled for choice!
Why should I purchase my South Side vacation package via Travelocity?
Incredible savings, loads of inspiring destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.
Can I save money on my South Side car rental if I combine it with hotels and flights?
Definitely — and if you also add an experience or activity to your South Side vacation package, you'll save some more. With a package from Travelocity, you can find things to do in the area that are just right for you. Then, jump in your rental car and work your way through the list. Geneva State Park is one must-see sight to visit. You'll find it 110 mi from South Side.
What is there to do in South Side?
Follow the lead of fellow travelers and head to Rex Theater. No visit to South Side would feel complete without a stop at this notable attraction.

Photos of local treasures

Browse South Side vacation photos for more inspiration

A park with autumn trees, a bridge, and a building labeled UPMC in the background.
A street with historic buildings, including a law office and a Ukrainian home.
A carousel with horses and riders, a fire truck, and a building with windows.
A staircase leading up to a building with yellow autumn leaves, surrounded by greenery and a clear sky.
The Cheesecake Factory restaurant with outdoor seating and a garden area.

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