Upper Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Upper Hill
Price found within the past 48 hours. Click for updated prices.
My Place Hotel - Pittsburgh North/Monaca, PA
Price was CA $839, price is now CA $802 per person
CA $802
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (412 reviews)
very clean room, staff was very courteous
Reviewed on Feb 23, 2026
Omni William Penn Hotel
Downtown Pittsburgh
Price was CA $1,596, price is now CA $1,396 per person
CA $1,396
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,960 reviews)
Excellent stay in downtown. Parking is very close to the building also. Near many great restaurants as well
Reviewed on Mar 15, 2026
Where to stay in Upper Hill
Find the best Upper Hill areas and neighborhoods for the activities you enjoy most. Learn more about Upper Hill
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(187 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.
Upper Hill Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Apr 5 to Apr 6
CA $170
CA $193 total
Apr 5 - Apr 6
includes taxes & fees
8.2/10 Very Good! (3,438 reviews)
Rooms were SMALL.
Reviewed on Mar 17, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Apr 1 to Apr 2
CA $152
CA $176 total
Apr 1 - Apr 2
includes taxes & fees
8.4/10 Very Good! (1,480 reviews)
The staff were all very friendly and welcoming. The rooms and all of the public areas were very clean and well maintained. I will say the room layout was a bit awkward. Having the hangers for clothes right above the refrigerator allowed for the clothes to constantly get in the way of closing the ...
Reviewed on Mar 16, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Mar 21 to Mar 22
CA $218
CA $248 total
Mar 21 - Mar 22
includes taxes & fees
9.2/10 Wonderful! (1,963 reviews)
This stay has set the standard!! The Omni William Penn was an amazing experience. In addition to being simply stunning, great architecture, and perfectly located for what we needed, it offered many amenities. We were there for a week and hated to leave. First, every single team member was nothing ...
Reviewed on Mar 17, 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 Upper Hill
PNC Park
4.5/5(67 reviews)
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
PPG Paints Arena
5/5(80 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.
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.
Things to do
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
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.