
Oakwood Vacation Packages
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Top Holiday Package Deals in Oakwood
Price found within the past 48 hours. Click for updated prices.

Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,549, price is now CA $1,270 per person
CA $1,270
per person
Oct 10 - Oct 12
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8/10 Very good! (302 reviews)
I traveled to Pittsburgh for a Pirates game with a friend back in June. This place was perfect for us. We rented 3D. It was a clean, a two bedroom, two bath apartment, and six twin beds with an easy 15-minute walk to the PNC Park. Crossing the Roberto Clemente bridge was a blast with all the fans. Also Stay Pittsburgh is walking distance to the Monongahela Incline (drops you off in Mount Washington) and the Market Square where I relaxed with a Primanti Bros sandwich.
The price was way better than a single hotel room. Truth be told it’s not a Ritz Carlton but like I said it’s walking distance to everything.
Some issues we experienced – their “About this property” promotes Street parking available, so we thought FREE street parking. This is not the case, just an FYI you can park on the street but it’s very expensive. They should update their “About this property” to state PAID street parking available or state there are many parking garages in the area that you can park for $25-$30 dollars a night which is not bad but people should know.
Although the place is clean, and an awesome location, things like the towels and pots and pans seem like they are from the 1970s. Also, some aging towel racks and faucets. I didn’t mind just something you should beware.
Overall, if I ever return to Pittsburgh I would definitely stay there again even with my wife, of course with an apartment that does not have twin beds. Remember location, location, location is key!
Reviewed on Jul 13, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $2,129, price is now CA $1,681 per person
CA $1,681
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.4/10 Very good! (1,078 reviews)
Great place to stay, clean, comfortable, helpful staff, great location very walkable. Very nice long weekend with the family went to a game and some museums and restaurants all within walking distance.
Reviewed on Jul 14, 2026

The Atterbury Hotel, Autograph Collection
Downtown Pittsburgh
Price was CA $1,888, price is now CA $1,552 per person
CA $1,552
per person
Aug 31 - Sep 5
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,004 reviews)
What a beautiful place! Clean room, great shower, sink, and toilet. Very comfy bed.
Free breakfast, and you pick off a menu, while you're waited on. I had the smoked salmon Benedict eggs. It was built in 1909 and is all marble floors and some walls. Just gorgeous! Very friendly staff.
I highly recommend it.
Reviewed on Jul 14, 2026

Springhill Suites by Marriott Pittsburgh North Shore
North Shore
Price was CA $1,833, price is now CA $1,529 per person
CA $1,529
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.4/10 Very good! (1,002 reviews)
Great spot and close to bars and restaurants!!! Free breakfast was great and filling.
Reviewed on Jul 14, 2026

Hilton Garden Inn Pittsburgh Airport
Price was CA $1,583, price is now CA $1,370 per person
CA $1,370
per person
Aug 31 - Sep 5
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,003 reviews)
The staff didn’t clean my room as advertised every day. I had to ask to have room cleaned. Or one day coffee was not relished. Other than that it was excellent, front desk staff were superb
Reviewed on Jul 9, 2026
Where to stay in Oakwood
Find the best Oakwood areas and neighborhoods for the activities you enjoy most. Learn more about Oakwood

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.
Oakwood Hotel Deals

Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jul 19 to Jul 20
CA $189
CA $215 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (3,623 reviews)
"This property is old and let's just say needs updated"
Reviewed on Jul 15, 2026

The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Jul 19 to Jul 20
CA $201
CA $229 total
Jul 19 - Jul 20
includes taxes & fees

Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Aug 3 to Aug 4
CA $190
CA $217 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (806 reviews)
"Nice service, very clean and adjacent to the Pitt campus."
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 Oakwood 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.










