South Side Vacation Packages

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Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kasa South Side Pittsburgh

Kasa South Side Pittsburgh

4 out of 5
South Side Flats
per person
Jul. 19 - Jul. 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (55 reviews)
Directions regarding parking were at times confusing...counter tops were sticky...had to clean before using...otherwise everything was as expected

Reviewed on Jun. 2, 2024

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,003 reviews)
Easy check inn never went to the front desk to check in or out

Reviewed on Jun. 3, 2024

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Modern clean hotel .

Reviewed on May 13, 2024

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (2,724 reviews)
The hotel was very easy to get to from out of town, conveniently located a very short walk across the bridge to both Acrisure and PNC, stadiums and bars and restaurants downtown. Beautiful park and scenery. Nothing was too far to walk to or subway was super convenient and free. Staff were friendly and knowledgeable. Saur at the concierge‘s desk was absolutely wonderful. You can tell that he really likes helping people. Very kind man. The only thing and it’s totally personal is the brown colour in the hallways and curtains could be updated to a more fun colour. The gray on the 4th floor was a little better of a choice. Thank you for a great weekend

Reviewed on Jun. 3, 2024

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Jul. 19 - Jul. 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.2/10 Very Good! (659 reviews)
Staff at front desk were very friendly and helpful. Hotel was clean. Although room was small it had everything we needed. Would stay again!

Reviewed on Jun. 3, 2024

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
South Shore showing a city, landscape views and a river or creek

Mount Washington

Consider a visit to Patrick Fagan Overlook and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station.

Find hotel + flight trips in Mount Washington

South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
2.5 out of 5
20 S 10th St, Pittsburgh, PA
Fully refundable
The price is CA $159 per night from Jun. 9 to Jun. 10
CA $159
CA $181 total
includes taxes & fees
Jun 9 - Jun 10
7/10 Good! (1,008 reviews)
"Excellent front desk staff, attentive and ready to help. Extremely quiet and comfortable hotel with clean common areas. Had to visit 4 floors to find a working ice maker. Pool closed at 10pm. Very secure and well lit area. We stayed on a night when the hotel was completely booked, yet it was clean ..."

Reviewed on Jun. 2, 2024

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
HYATT house Pittsburgh-South Side
HYATT house Pittsburgh-South Side
3 out of 5
2795 S Water St, Pittsburgh, PA
Fully refundable
The price is CA $191 per night from Jun. 30 to Jul. 1
CA $191
CA $217 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,001 reviews)
"This was a great venue for a family wedding! The suites are large and comfortable."

Reviewed on May 27, 2024

HYATT house Pittsburgh-South Side
Omni William Penn Hotel
Omni William Penn Hotel
4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Jun. 30 to Jul. 1
CA $238
CA $271 total
includes taxes & fees
Jun 30 - Jul 1
9/10 Wonderful! (1,335 reviews)
"Nice hotel"

Reviewed on Jun. 3, 2024

Omni William Penn Hotel
See all 1,560 properties in South Side
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only CA $1,069, actually! By combining hotels, flights and car rentals into a customized package, your getaway to South Side is just clicks away.
How do I get a cheap travel package to South Side?
Search for flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a South Side vacation package. It’s as easy as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 properties around the world to select from, you won’t be short of choice.
Where should I stay in South Side?
Travelers come from all over the world to experience Acrisure Stadium and PNC Park in South Side. Book a room near these must-see attractions to make sightseeing a breeze.
What are the top hotels in South Side?
If it’s your first visit to South Side, lock in a room at Kasa South Side Pittsburgh or SpringHill Suites by Marriott Pittsburgh Southside Works. Both hotels offer friendly service and are favorites with lots of travelers.
How far in advance should I book my South Side vacation?
Reward yourself with the widest variety at the cheapest prices by booking your South Side vacation early. Airlines generally publish flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so it’s never a bad time to book your dream vacation!
What does an Expedia South Side travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you’ve made your booking, add on a few tours and activities and watch your savings stack up. When it comes to crafting your South Side break, you’re in charge!
What should I know before booking a South Side travel package?
You’ll score impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together just makes things easier. So why waste your time or money? Whether you’re organizing a ritzy romantic getaway or a low-cost family road trip, explore our package deals today.
Can I choose my airline with a South Side Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to South Side in business or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my South Side vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or amend your South Side vacation package at no cost if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Need more information? Look up our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in South Side

Image for PNC Park

PNC Park

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

PNC Park
Image for Acrisure Stadium

Acrisure Stadium

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium
Image for University of Pittsburgh

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh

What to do in South Side

Image for Pittsburgh's Hidden Treasures Tour

Pittsburgh's Hidden Treasures Tour

CA $80
Per adult
Pittsburgh's Hidden Treasures Tour
See all activities in South Side

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.