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 $1,342, price is now CA $1,101 per person
CA $1,101
per person
Sep 18 - Sep 21
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8/10 Very good! (310 reviews)
Very responsive, great location, awesome hosts! 10/10 would recommend.
Reviewed on Jul 31, 2026
South Broadway Manor
Price was CA $1,489, price is now CA $1,286 per person
CA $1,286
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9.8/10 Exceptional! (115 reviews)
Pat went above and beyond. First of all, we were late and only checked in at about 3:00 in the morning. She still made herself available and provided access at this incredibly late hour. This property is super cool. It has lots of history and it feels like you're staying in a historical property. Each of the rooms is themed and has unique artifacts and decorations. Very cool experience and highly recommended!!
Reviewed on Jul 26, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,266, price is now CA $1,130 per person
CA $1,130
per person
Sep 18 - Sep 21
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,583 reviews)
Every time I made a request that I need something or I need to have something fixed, the staff helped me resolve the problem. Very good.
Reviewed on Aug 1, 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
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 $188 per night from Aug 9 to Aug 10
CA $188
CA $214 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (3,689 reviews)
"Room was extremely dated including no fan in bathroom, minimal toiletries compared to most Wyndham hotels and very limited plug ins. Elevator's extremely slow Location was excellent though"
Reviewed on Aug 1, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 2 to Sep 3
CA $193
CA $220 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (2,089 reviews)
"Beautiful hotel in a very scenic area along the river! Excellent service from staff!"
Reviewed on Aug 2, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
The price is CA $251 per night from Aug 9 to Aug 10
CA $251
CA $286 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (2,053 reviews)
"Bar was wonderful"
Reviewed on Jul 31, 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.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $73
per adult
100% of travellers recommend
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.