Southwest Pennsylvania Vacation Packages 2026 from $532

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Your Southwest Pennsylvania Vacation

Make the most out of your next break with a tailor-made vacation package to Southwest Pennsylvania. Acquaint yourself with the rich history and all the other things that make this destination an unforgettable experience. With so much to see and do on a trip to Southwest Pennsylvania, it can be hard to know where to start. Kick off your travels in Pittsburgh at Great Allegheny Passage and Kennywood — two popular attractions here. Another great city to add to your itinerary is Washington. Be sure not to miss Hollywood Casino at the Meadows and Tanger Outlet Center. From the instant you book your Southwest Pennsylvania vacation to when you get back home, Expedia will be with you every step of the way.

The Latest Southwest Pennsylvania 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 10 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 10 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 10 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

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Where to stay in Southwest Pennsylvania

Find the best Southwest Pennsylvania areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Pennsylvania

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.

Stay near popular Southwest Pennsylvania attractions

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

Acrisure Stadium

9.2/10 (3,391 reviews)

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

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An indoor ice hockey rink with a scoreboard, audience seating, and hockey players on the ice.

PPG Paints Arena

9.2/10 (2,088 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.

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PNC Park

9.4/10 (3,076 reviews)

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

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A steel structure with a lattice design, reflecting a modern building with large windows.

David L Lawrence Convention Center

8.4/10 (705 reviews)

Learn about the events happening at David L Lawrence Convention Center during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.

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A city skyline at dusk with a river and a bridge.

Rivers Casino

8.6/10 (1,596 reviews)

Why not try your luck with a visit to Rivers Casino during your travels in Pittsburgh? Amble around this vibrant area's riverfront or experience its acclaimed theater scene.

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Seven Springs Mountain Resort

9.0/10 (329 reviews)

Hit the slopes in Champion with a visit to Seven Springs Mountain Resort. Take in the art scene and countryside in this romantic area.

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The Mall at Robinson

8.6/10 (518 reviews)

During your trip to Pittsburgh, you can do some window-shopping at The Mall at Robinson. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

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Sri Venkateswara Temple

8.8/10 (187 reviews)

After visiting Sri Venkateswara Temple, make a plan to see the other sights and activities in Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.

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What to do in Southwest Pennsylvania

BYOB Historically Hilarious Trolley Tour of Philadelphia

$49

per adult

94% of travellers recommend

Museum of Illusions Philadelphia Admission Ticket

$29

per adult

94% of travellers recommend

Philadelphia Haunted Halloween Tour: Terror Beyond the Walls

$65

per adult

See all activities in Southwest Pennsylvania

Southwest Pennsylvania Hotel Deals

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

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA

Fully refundableReserve now, pay when you stay

$109 nightly

$124 total

Nov 3 - Nov 4

Total with taxes and fees

8.8/10 Excellent! (1,250 reviews)

"Such a lovely hotel. So close to everything. Rooms were spotless, staff were friendly, parking was abundant, and always felt safe as mother traveling with small children. When we go back to Pittsburgh this is where we will stay."

Reviewed on Oct 6, 2026

See all 3,246 properties in Southwest Pennsylvania

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.