
South Side Mountain Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Flight and Mountain hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.

Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $1,152, price is now CA $1,010 per person
CA $1,010
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.4/10 Very Good! (100 reviews)
Beautiful building, friendly staff, gym was great. It has everything you need. Walking distance to everything and the valet service is top notch. So quiet inside the apartment too, you don't hear any neighbors or noise from upstairs. Thanks again, we will stay here again when visiting Pittsburgh.
Reviewed on May 18, 2026

The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,734, price is now CA $1,368 per person
CA $1,368
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 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

Renaissance Pittsburgh Hotel
Downtown Pittsburgh
Price was CA $1,339, price is now CA $1,164 per person
CA $1,164
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (1,011 reviews)
The view from riverside is priceless
Reviewed on May 17, 2026


Fairmont Pittsburgh
Downtown Pittsburgh
Price was CA $1,533, price is now CA $1,342 per person
CA $1,342
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,003 reviews)
The room and amenities were excellent but the mattress was worn out had a large depression on one side.
Reviewed on May 14, 2026
3 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.

Renaissance Pittsburgh Hotel
Downtown Pittsburgh
Price was CA $1,339, price is now CA $1,164 per person
CA $1,164
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (1,011 reviews)
The view from riverside is priceless
Reviewed on May 17, 2026

The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,734, price is now CA $1,368 per person
CA $1,368
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 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

4 Night Mountain holidays in South Side
Price found within the past 48 hours. Click for updated prices.

Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,352, price is now CA $1,088 per person
CA $1,088
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8/10 Very Good! (280 reviews)
This was a perfect arrangement for our short visit to Pittsburgh. Clean and functional.
Reviewed on May 20, 2026

The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,929, price is now CA $1,493 per person
CA $1,493
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 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

Traveler's Rest Hotel
South Side Flats
Price was CA $2,049, price is now CA $1,725 per person
CA $1,725
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9.6/10 Exceptional! (99 reviews)
This might be the coolest place I have ever stayed. Rooms are small (used to be a hostel) but spotless as is the rest of the hotel. Great history behind this building. Very comfortable sitting in the great room conversing with others. The peacefulness was in large part due to this being a TV free hotel.
Reviewed on Nov 17, 2025
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







