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.
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,178, price is now CA $982 per person
CA $982
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.4/10 Very good! (1,078 reviews)
Unclean toilet bowl, showel gel not refilled, no slippers, washroom smaller than a printing room in office space, just not comfortable for the price we paid. And in the parking they said there's only valet parking but didnt mention the price of $45. Just a scam and cheap mentality from such a huge institution.
Reviewed on Jul 12, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $2,475, price is now CA $1,954 per person
CA $1,954
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Property is a beautiful, historic building in a convenient location off the freeway. Our rooms were spacious, clean, and comfortable with the exception of no central air. A loud, mobile air unit was in two of the rooms. The blinds in one room could not close because of a missing wand. Also the roku was not working. Keep in mind hotel room is near train tracks. Staff was kind enough to meet us at the parking area door to let us into the building so that we could conveniently check in (some parking is near an amtrak station).
Reviewed on Jul 10, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,704, price is now CA $1,455 per person
CA $1,455
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,551 reviews)
Super clean. Comfy beds. Staff was wonderful!
Reviewed on Jul 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 $190 per night from Jul 19 to Jul 20
CA $190
CA $216 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (3,630 reviews)
"Room is a little outdated and could use some work but other than that it was great. Perfect location, staff is great and helpful. Pool was nice as well."
Reviewed on Jul 12, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Aug 5 to Aug 6
CA $194
CA $222 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (1,960 reviews)
"Had to walk through casino to get to parking garage big inconvenience so don’t forget anything from your car"
Reviewed on Jul 11, 2026
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jul 19 to Jul 20
CA $191
CA $218 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (800 reviews)
"Clean room, good location"
Reviewed on Jul 12, 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.
Stay near popular Highland Park attractions
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $79
per adult
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $46
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.