Southwest Pennsylvania Vacation Packages 2026 from $645

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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.

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

$645

per person

Nov 13 - Nov 18

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Pittsburgh (PIT)

8.6/10 Excellent! (228 reviews)

First I would like to say the Hotel was very Beautiful. I do love the history of this hotel. I can see why someone would want their wedding here. The check in process could be better. I didn't feel comfortable sending someone my license via internet to check in. In this world with Data Breeches it's just not safe and I don't feel comfortable. So- it takes a little longer to check in at the desk, it's fine. The 1st room we had unfortunately, the air conditioner was not operating properly. The Staff concierge was so nice enough to move our room. The place was beautiful and spotless. We had everything we needed for a fun family visit. The gym was very well equipped, and a plethora of weights. I was very pleased. The staff was very kind and always welcoming. It was a pleasurable stay. We will visit again. Thank you.

Reviewed on Sep 7, 2026

Stay Pittsburgh

Downtown Pittsburgh

$956

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8/10 Very Good! (325 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$840

per person

Oct 12 - Oct 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Staff extremely helpful and friendly , bar on site great food and service

Reviewed on Sep 6, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

$748

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,175 reviews)

EVEN Hotel Pittsburgh Downtown by IHG

Downtown Pittsburgh

$714

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

8.8/10 Excellent! (1,090 reviews)

Rooms were small but the bed was comfortable. The air conditioning unit was screaming the entire stay. We were just there two nights and were barely in the room, but yeah - I was sort of shocked at how loud it was. The seating area in the lobby is really nice.

Reviewed on Sep 8, 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 bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.

North Side

1 out of top 10 points of interest in this area

If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.

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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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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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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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

Museum of Illusions Philadelphia Admission Ticket

$29

per adult

100% of travellers recommend

BYOB Historically Hilarious Trolley Tour of Philadelphia

$49

per adult

94% of travellers recommend

Polaris Slingshot Rental-Philadelphia, PA

$250

per traveler

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

$165 nightly

$188 total

Oct 1 - Oct 2

Total with taxes and fees

8.4/10 Very Good! (3,783 reviews)

"The location was perfect in getting to the baseball and football stadium and the beautiful downtown."

Reviewed on Sep 8, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA

Fully refundableReserve now, pay when you stay

$106 nightly

$121 total

Sep 20 - Sep 21

Total with taxes and fees

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

$152 nightly

$173 total

Oct 5 - Oct 6

Total with taxes and fees

9.4/10 Exceptional! (2,289 reviews)

"Our room was not clean. The toilet was dirty. There were two different earrings found on the floor. The air conditioner was not working. We asked for help from front desk. They sent someone up but ultimately nothing was done. We not offered a different room as I requested. It was so uncomfortable. ..."

Reviewed on Sep 8, 2026

See all 3,206 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.