Southwest Pennsylvania Vacations from $359
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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.
Stay Pittsburgh
Downtown Pittsburgh
Price was $771, price is now $553 per person
$553
per person
Jun 4 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (262 reviews)
Location is great. Place was spacious and clean. Check-in process was all online. I was pleasantly surprised because of how affordable it was!
Reviewed on Apr 19, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Save 100% on your flight
Price was $943, price is now $681 per person
$681
per person
Jun 4 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.4/10 Very Good! (87 reviews)
Great historical building and spacious apartment hotel. Walkable to downtown area, Strip District and all sports facilities. Spacious and clean hotel
Reviewed on Apr 20, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $771, price is now $570 per person
$570
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.
Reviewed on Apr 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southwest Pennsylvania
View all tripsWhere to stay in Southwest Pennsylvania
Find the best Southwest Pennsylvania areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Pennsylvania
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)
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.
Discover the most popular places to visit in Southwest Pennsylvania
PNC Park
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
Acrisure Stadium
Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
What to do in Southwest Pennsylvania
Center City Philadelphia Food Tour with Reading Market
$59
per adult
88% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
$49
per adult
100% of travellers recommend
Southwest Pennsylvania Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Apr 26 to Apr 27
$181 total
Apr 26 - Apr 27
Total with taxes and fees
8.2/10 Very Good! (3,485 reviews)
The property was okay for what we needed to be in town for. The pool was not in service. The restaurant wasn't kid friendly. The rooms were small.
Reviewed on Apr 20, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $261 total per night from Apr 30 to May 1
$261 total
Apr 30 - May 1
Total with taxes and fees
9.2/10 Wonderful! (1,998 reviews)
.
Reviewed on Apr 21, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $183 total per night from Apr 26 to Apr 27
$183 total
Apr 26 - Apr 27
Total with taxes and fees
8.2/10 Very Good! (1,209 reviews)
Clean, Lobby Restaurant was good, breakfast was ok
Reviewed on Apr 20, 2026
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.
Find the Best Southwest Pennsylvania Vacation Packages
Southwest Pennsylvania Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Pittsburgh Intl. Airport (PIT) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
