Highland Park Vacation Packages
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Top Holiday Package Deals in Highland Park
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,498, price is now CA $1,175 per person
CA $1,175
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
7.8/10 Good! (276 reviews)
Was a nice place to stay for the night and it was quiet the night I stayed. Host was easy to get a hold of.
Reviewed on May 11, 2026
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,573, price is now CA $1,184 per person
CA $1,184
per person
Jun 21 - Jun 26
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.2/10 Very Good! (3,530 reviews)
Excellent room for my stay. the mini-suite was clean and comfortable. Friendly staff at check-in. Couldn't ask for more from a short weekend home from home.
Reviewed on May 11, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,909, price is now CA $1,483 per person
CA $1,483
per person
Jun 21 - Jun 26
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,058 reviews)
Good central location and friendly staff…
Reviewed on May 12, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $1,613, price is now CA $1,281 per person
CA $1,281
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.4/10 Very Good! (100 reviews)
It was a little tricky finding the parking lot but once I was there the apartment was beautiful, well stocked, and very comfortable.
Reviewed on May 12, 2026
Renaissance Pittsburgh Hotel
Downtown Pittsburgh
Price was CA $2,405, price is now CA $1,910 per person
CA $1,910
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
9/10 Wonderful! (1,005 reviews)
Beautiful hotel, pleasant stay and will be back.
Reviewed on May 11, 2026
Where to stay in Highland Park
Find the best Highland Park areas and neighborhoods for the activities you enjoy most. Learn more about Highland Park
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(190 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.
Highland Park Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from May 27 to May 28
CA $226
CA $258 total
May 27 - May 28
includes taxes & fees
8.2/10 Very Good! (3,518 reviews)
Clean room, nice pool area and hot tub and the view. The shower was hot with a good pressure. So my husband likes IPA beers. The event we attebded at the hotel did not have any so since we were staying we called to see what time the bar closed. The front desk staff said 1 am. We went down to the ...
Reviewed on May 11, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from May 25 to May 26
CA $196
CA $223 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,710 reviews)
Excellent
Reviewed on May 13, 2026
Hyatt Regency Pittsburgh International Airport
710 Aviation Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 17 to May 18
CA $231
CA $264 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,657 reviews)
A little pricey but I paid for the incredible convenience. Very clean room. Hotel staff including the bar staff was super friendly and helpful. Shuttle to airport was perfectly timed for us to get to our flight. Great experience. Will stay again if our flight leaves at 4a again.
Reviewed on May 13, 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.
Discover the most popular places to visit in Highland Park
PNC Park
4.5/5(69 reviews)
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
University of Pittsburgh
4.5/5(36 reviews)
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.
Acrisure Stadium
4.5/5(94 reviews)
Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
CA $40
per adult
80% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
CA $81
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.