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.
South Broadway Manor

South Broadway Manor

3 out of 5
Price was $837, price is now $733 per person
$733
per person
Dec 23 - Dec 25
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls, an off-leash area, and litter boxes. Enjoy the hot tub and conveniences like a terrace and laundry facilities.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,156, price is now $993 per person
$993
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the steam room and perks like free WiFi. Valet parking, a 24-hour business center, and a coffee shop are also offered.
Homewood Suites by Hilton Pittsburgh Southpointe

Homewood Suites by Hilton Pittsburgh Southpointe

3 out of 5
Price was $1,083, price is now $952 per person
$952
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Pittsburgh (PIT)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $1,005, price is now $897 per person
$897
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. A terrace, a snack bar/deli, and luggage storage are also on offer.

Top South Side hotels deals

SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
2950 S Water St Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Dec 7 - Dec 8
Total with taxes and fees
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
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
$97 nightly
The price is $111 total per night
$111 total
Nov 30 - Dec 1
Total with taxes and fees
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
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
$124 nightly
The price is $141 total per night
$141 total
Nov 23 - Nov 24
Total with taxes and fees
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
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $123 total per night
$123 total
Nov 22 - Nov 23
Total with taxes and fees
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 coffee shop, and a lobby fireplace are also offered.
Pet friendly
Parking included
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
$130 nightly
The price is $148 total per night
$148 total
Nov 18 - Nov 19
Total with taxes and fees
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
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd Coraopolis PA
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $91 total per night
$91 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
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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.
See properties

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 $733. 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

Large stainless steel brewing tanks with logos and text, set against a building with arched windows and a brick facade.
A theater with a marquee reading "Southside Works" and a brick building with a large tree in front.
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.

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