Osborne Vacation Packages
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Top Osborne Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport
Price was CA $1,424, price is now CA $1,144 per person
CA $1,144
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
In the room, under the chair was dirty clothing left behind by someone else. No coffee pot in room. Facility is nice, the room was otherwise nice, staff were super friendly.
Reviewed on Jun 13, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,789, price is now CA $1,296 per person
CA $1,296
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,527 reviews)
Nothing stood out about this hotel. I would not stay here again. The room was very small and if there are amenities we didn’t know about them.
Reviewed on Jun 14, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $3,385, price is now CA $2,668 per person
CA $2,668
per person
Jul 26 - Jul 31
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.
Reviewed on Apr 10, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,876, price is now CA $1,484 per person
CA $1,484
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,065 reviews)
Valet parking was an easy process.
Reviewed on Jun 12, 2026
Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,906, price is now CA $1,535 per person
CA $1,535
per person
Aug 22 - Aug 29
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8/10 Very Good! (290 reviews)
Third time staying at the property. Minor issue with the elevator being out of service for a couple of days, but otherwise another pleasant stay. Will definitely be back when I’m in the area.
Reviewed on Jun 14, 2026
Osborne 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 Jul 9 to Jul 10
CA $188
per night
Jul 9 - Jul 10
8.2/10 Very Good! (3,636 reviews)
"Rooms are very outdated and small. Had great views on the 24th floor, but it was so hot in the room. The walls are thin. There was constant loud conversations in the presidential suite and lots of foot traffic. The bathroom is tiny. The beds are super small and truly only comfortable for one adult. ..."
Reviewed on Jun 14, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from Jun 29 to Jun 30
CA $243
per night
Jun 29 - Jun 30
9.2/10 Wonderful! (2,032 reviews)
"Wonderful place."
Reviewed on Jun 12, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun 28 to Jun 29
CA $181
per night
Jun 28 - Jun 29
9.4/10 Exceptional! (1,829 reviews)
"Would definitely stay again. Close to everything"
Reviewed on Jun 14, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
