South Shore Vacation Packages 2026 from $532

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Your South Shore Vacation

Avoid the hassle of travel planning with a South Shore vacation package. With all the details organized before you go away, all that's left for you to do is enjoy this riverside neighborhood's cycling, views and walking. Start your trip to South Shore by heading to nearby attractions such as Acrisure Stadium, University of Pittsburgh and PNC Park. Stop daydreaming and start doing. When it's time to book your next vacation to South Shore, Expedia is here to help.

The Latest South Shore Vacation Packages

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

The Inn on Negley

Shadyside

$532

per person

Nov 14 - Nov 16

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Pittsburgh (PIT)

10/10 Exceptional! (225 reviews)

This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.

Reviewed on Sep 30, 2026

Stay Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

$612

per person

Dec 18 - Dec 21

found 9 hours ago

Roundtrip flight included

New Orleans (MSY) to Pittsburgh (PIT)

8/10 Very Good! (334 reviews)

Oakmont Inn

Plum

$689

per person

Nov 6 - Nov 8

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

10/10 Exceptional! (38 reviews)

Very quiet and incredibly clean! We absolutely loved the place!

Reviewed on Sep 27, 2026

The Oaklander Hotel, Autograph Collection

Oakland

$638

per person

Dec 18 - Dec 21

found 9 hours ago

Roundtrip flight included

New Orleans (MSY) to Pittsburgh (PIT)

9.2/10 Wonderful! (838 reviews)

I've been to other Autograph Hotels _-last one was in Georgia outside Milton. They always had a place where I could buy gum, lifesavers, or other things that I might have forgotten. When I asked at the desk, they sent me at night to the 7-11. They also were not helpful when I wanted to cancel the last night and would not give me any information on who I booked it with. After I sat on the phone with A-I for 20 minutes and got it, and went to the desk to give it, theye "remembered" that YES, I did book through Hotels.com. Little things mean a lot.

Reviewed on Oct 3, 2026

Hyatt Place Pittsburgh-North Shore

North Shore

$987

per person

Dec 18 - Dec 21

found 9 hours ago

Roundtrip flight included

New Orleans (MSY) to Pittsburgh (PIT)

8.8/10 Excellent! (1,269 reviews)

The hotel is a little dated with limited views of the city. It states a restaurant on site, but there is no restaurant or bar as stated on their website. The complimentary breakfast was good but they close the restaurant right at 9am. Coffee was not available after the 9am closing since everything was removed by the staff. The staff was great and they reported the hotel is being renovated starting in November 2026. The rooms definitely need updating and our sofa had a lot of stains on it. There is no microwave in the room. A decent place to stay if you are going to any of the stadiums in town. Close to Jason Aldean's kitchen and bar.

Reviewed on Oct 5, 2026

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore

A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

2 out of top 10 points of interest in this area

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.

The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.

A street with a Starbucks and a plaza with colorful steps.

Strip District

Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.

A courtyard with a fountain, brick walls, and trees.

Shadyside

Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.

South Shore Hotel Deals

Sheraton Pittsburgh Hotel at Station Square

300 West Station Square Drive Pittsburgh PA

Fully refundableReserve now, pay when you stay

$161 nightly

$183 total

Nov 2 - Nov 3

Total with taxes and fees

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$124 nightly

$141 total

Oct 22 - Oct 23

Total with taxes and fees

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

$149 nightly

$170 total

Nov 5 - Nov 6

Total with taxes and fees

9.4/10 Exceptional! (2,402 reviews)

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Reviewed on Oct 6, 2026

See all 2,032 properties in South Shore

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 Shore attractions

A bridge with ornate towers and a cityscape in the background.

Station Square

8.6/10 (1,102 reviews)

You can do some window-shopping at Station Square during your trip to Pittsburgh. Experience the entertainment choices and acclaimed theater scene in this vibrant area.

See properties

A river with a bridge, a parking lot, and a small building.

Monongahela Incline

9.0/10 (402 reviews)

Spectacular views of the Pittsburgh cityscape await at the top of the steepest funicular railway in the United States.

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Highmark Stadium

8.6/10 (12 reviews)

Catch an event at Highmark Stadium during your trip to Pittsburgh. Amble around this vibrant area's riverfront or attend a sporting event.

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Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

$29

per adult

86% of travellers recommend

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13

per adult

Pittsburgh: Beauty of the Burgh Bike Tour

$59

per adult

94% of travellers recommend

See all activities in Pittsburgh

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

South Shore Vacations from $532

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your South Shore Vacation

The Latest South Shore Vacation Packages

The Inn on Negley

Stay Pittsburgh

Oakmont Inn

The Oaklander Hotel, Autograph Collection

Hyatt Place Pittsburgh-North Shore

Where to stay in South Shore

Downtown Pittsburgh

North Shore

Oakland

Strip District

Shadyside

South Shore Hotel Deals

Sheraton Pittsburgh Hotel at Station Square

Wyndham Grand Pittsburgh Downtown

The Landing Hotel at Rivers Casino

Stay near popular South Shore attractions

Station Square

Monongahela Incline

Highmark Stadium

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh: Beauty of the Burgh Bike Tour