Overbrook Vacation Packages
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Top Holiday Package Deals in Overbrook
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,313, price is now CA $1,039 per person
CA $1,039
per person
Jul 26 - Jul 31
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8/10 Very Good! (290 reviews)
Had an entire apartment for 1 person. Had everything necessary and highly recommend. Great communication.
Reviewed on Jun 8, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,787, price is now CA $1,295 per person
CA $1,295
per person
Aug 22 - Aug 29
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,527 reviews)
Super decorative, cozy, and the rooms were super clean! Valet was quick and convenient!
Reviewed on Jun 8, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,879, price is now CA $1,487 per person
CA $1,487
per person
Aug 22 - Aug 29
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,065 reviews)
Front desk is awesome! Sink barely drained water and there were hairs in bathtub and on most of the bath towels... other than that it was great.
Reviewed on Jun 11, 2026
Americas Best Value Inn Pittsburgh Airport
Price was CA $1,422, price is now CA $1,143 per person
CA $1,143
per person
Aug 22 - Aug 29
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
Free shuttle ,from airport , budget friendly hotel. It was okay and decent enough . Walking distance to food n gas station n other places.
Reviewed on Jun 11, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $1,611, price is now CA $1,313 per person
CA $1,313
per person
Jul 26 - Jul 31
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.4/10 Very Good! (122 reviews)
This was a great option for us and we would most definately stay here again! It is beautiful and perfect for a weekend stay.
Reviewed on Jun 12, 2026
Where to stay in Overbrook
Find the best Overbrook areas and neighborhoods for the activities you enjoy most. Learn more about Overbrook
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.
Overbrook Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 9 to Jul 10
CA $208
CA $237 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very Good! (3,629 reviews)
"Clean room and lounge was nice"
Reviewed on Jun 12, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Jun 28 to Jun 29
CA $236
CA $269 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (2,030 reviews)
"Wonderful place."
Reviewed on Jun 12, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
The price is CA $200 per night from Jun 14 to Jun 15
CA $200
CA $228 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (1,822 reviews)
"The room was clean. It and the bathroom were very spacious. There was a ledge/desk that worked well for the one day that I had to work. There's an iron and hair dryer provided. Free parking is a huge perk this close to ballparks. Free breakfast lasted for 4 hours! It was decent and had lots of options. ..."
Reviewed on Jun 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.