South Side Vacation Packages 2026 from $606

South Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Pittsburgh Marriott City Center

Downtown Pittsburgh

$606

per person

Aug 13 - Aug 17

found 13 hours 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 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.

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh

$639

per person

Aug 13 - Aug 17

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a convenience store are also provided.

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

$726

per person

Sep 19 - Sep 23

found 4 hours ago

Roundtrip flight included

Philadelphia (PHL) to Pittsburgh (PIT)

A 24-hour gym, valet parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A hair salon, dry cleaning, and luggage storage are also on offer.

Hilton Garden Inn Pittsburgh Downtown

Downtown Pittsburgh

$802

per person

Aug 13 - Aug 17

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a business center, and express check-in are also offered.

Hyatt Regency Pittsburgh International Airport

$799

per person

Sep 19 - Sep 23

found 4 hours ago

Roundtrip flight included

Philadelphia (PHL) to Pittsburgh (PIT)

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 free airport shuttle. Self parking, a coffee shop, and express check-in are also offered.

Top South Side hotels deals

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$139 total

Jun 30 - Jul 1

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

20 S 10th St Pittsburgh PA

Free Cancellation

$100 nightly

$114 total

Jul 6 - Jul 7

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

600 Commonwealth Pl Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$141 total

Jul 19 - Jul 20

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

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$148 total

Jul 13 - Jul 14

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

Pittsburgh Marriott City Center

112 Washington Pl Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$135 total

Jul 19 - Jul 20

Total with taxes and fees

Pet friendly

Free WiFi

Placemakr Downtown Pittsburgh at The Pennsylvanian

1100 Liberty Ave Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$177 total

Jun 30 - Jul 1

Total with taxes and fees

A 24-hour gym, valet parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A hair salon, dry cleaning, and luggage storage are also on offer.

Kitchen

Washer

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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.

Popular places to visit

A baseball stadium with empty seats, a green field, and a city skyline in the background.

PNC Park

4.5/5(790 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

A stadium with a unique roof structure, a large Heinz sign, and a body of water in the foreground.

Acrisure Stadium

4.5/5(1,015 reviews)

Catch an event at Acrisure Stadium during your trip to Pittsburgh. Stroll along the riverfront or attend a sporting event in the area.

A statue of a man holding a child, with flags in the background.

PPG Paints Arena

4.5/5(609 reviews)

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

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 $606. 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.