Title: South Side Vacation Packages & Trips 2026 from CA $1,084 | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx6343590)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Side Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Hotel Indigo Pittsburgh East Liberty by IHG](https://images.trvl-media.com/lodging/10000000/9040000/9032700/9032700/112ecec9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

CA $1,084

per person

Feb 27 - Mar 6

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8/10 Very Good! (1,003 reviews)

Staff was extremely kind, friendly and helpful! The space was clean and beautiful! The breakfast was delicious!

Reviewed on Jan 11, 2026

![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,196

per person

Feb 27 - Mar 6

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.4/10 Very Good! (1,385 reviews)

The room and staff were great, breakfast was good as well. Dinner wasn’t as good. A very walkable location!

Reviewed on Jan 12, 2026

![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,316

per person

Feb 27 - Mar 6

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

7.6/10 Good! (37 reviews)

Nice rooms, beautiful building, good value, great location.

Reviewed on Jan 4, 2026

![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

CA $1,299

per person

Feb 27 - Mar 6

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.2/10 Very Good! (3,142 reviews)

Great location. Would stay there again. Rooms very clean and well maintained facility. $44 per day for parking at hotel. You can park right around the corner in Stanewicz (sp?) for $32 per day. Have fun in the Burgh!!

Reviewed on Jan 11, 2026

![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $1,606

per person

Feb 27 - Mar 6

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,003 reviews)

Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

## Ready to book your vacation to South Side?

Choose your dates

## South Side Hotel Deals

![Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/76c1ea4b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

20 S 10th St Pittsburgh PA

Fully refundable

CA $99

CA $113 total

Jan 19 - Jan 20

includes taxes & fees

7.2/10 Good! (1,011 reviews)

Every thing-was really good !!

Reviewed on Jan 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=914423&PinnedHotelID=914423&HadPinnedHotel=true&regionId=6343590)

![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $222

CA $253 total

Jan 23 - Jan 24

includes taxes & fees

9/10 Wonderful! (1,905 reviews)

Yes

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=2998&PinnedHotelID=2998&HadPinnedHotel=true&regionId=6343590)

![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $150

CA $171 total

Feb 3 - Feb 4

includes taxes & fees

8.2/10 Very Good! (3,344 reviews)

ever

Reviewed on Jan 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F02%2F2026&endDate=04%2F02%2F2026&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true&regionId=6343590)

[See all 1,816 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&regionId=6343590)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in South Side

![University of Pittsburgh](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473449-Pittsburgh.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### University of Pittsburgh

4.5/5(36 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area. 

[](https://expedia.ca/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction)

![PNC Park which includes a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/229000/229651-Pittsburgh.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### PNC Park

4.5/5(67 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

[](https://expedia.ca/PNC-Park-North-Shore.d6034814.Vacation-Attraction)

![PPG Paints Arena](https://mediaim.expedia.com/destination/2/68f5060bd63bff9d5010e3c2e4759aa8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### PPG Paints Arena

5/5(80 reviews)

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area. 

[](https://expedia.ca/PPG-Paints-Arena-Downtown-Pittsburgh.d6140367.Vacation-Attraction)

### What to do in South Side

![Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers](https://mediaim.expedia.com/localexpert/1228632/84aeeb47-bd3d-4277-b74c-be66fc259705.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

CA $27

per traveller

[](https://expedia.ca/things-to-do/adventurous-scavenger-hunt-in-bethlehem-by-zombie-scavengers.a1228632.activity-details)

![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/fb378b65-03b5-422b-84c6-ec829fe06b75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18

per adult

[](https://expedia.ca/things-to-do/pittsburgh-bar-hunt-party-through-pittsburgh-bar-crawl.a697587.activity-details)

![Make new friends as you learn the exciting history of whiskey in Pittsburgh](https://mediaim.expedia.com/localexpert/1359320/44c64494-c602-43ff-a552-b170c4986e13.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Whiskey Rebellion & Prohibition Tour

CA $62

per adult

[](https://expedia.ca/things-to-do/whiskey-rebellion-prohibition-tour.a1359320.activity-details)

[See all activities in South Side](https://expedia.ca/things-to-do/search?rid=6343590)

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- [Acrisure Stadium ](https://www.expedia.ca/Acrisure-Stadium-North-Shore.d6058087.Vacation-Attraction)
- [Andy Warhol Museum ](https://www.expedia.ca/Andy-Warhol-Museum-North-Shore.d6078695.Vacation-Attraction)
- [Carnegie Mellon University ](https://www.expedia.ca/Carnegie-Mellon-University-Squirrel-Hill.d6090503.Vacation-Attraction)
- [Carnegie Museum and Library ](https://www.expedia.ca/Carnegie-Museum-And-Library-Pittsburgh.d6215067.Vacation-Attraction)
- [Carnegie Museum of Art ](https://www.expedia.ca/Carnegie-Museum-Of-Art-Oakland.d6078685.Vacation-Attraction)
- [Carnegie Museum of Natural History ](https://www.expedia.ca/Carnegie-Museum-Of-Natural-History-Oakland.d6078701.Vacation-Attraction)
- [Carnegie Science Center ](https://www.expedia.ca/Carnegie-Science-Center-North-Side.d6078691.Vacation-Attraction)
- [Cathedral of Learning ](https://www.expedia.ca/Cathedral-Of-Learning-Oakland.d6269525.Vacation-Attraction)
- [Children's Museum of Pittsburgh ](https://www.expedia.ca/Childrens-Museum-Of-Pittsburgh-North-Side.d6078703.Vacation-Attraction)
- [Duquesne Incline ](https://www.expedia.ca/Duquesne-Incline-Duquesne-Heights.d6078687.Vacation-Attraction)
- [Heinz Hall ](https://www.expedia.ca/Heinz-Hall-Downtown-Pittsburgh.d6163670.Vacation-Attraction)
- [Kennywood ](https://www.expedia.ca/Kennywood-Pittsburgh.d6193719.Vacation-Attraction)
- [Manor Theatre ](https://www.expedia.ca/Manor-Theatre-Squirrel-Hill-South.d553248621532660405.Vacation-Attraction)
- [Market Square ](https://www.expedia.ca/Market-Square-Downtown-Pittsburgh.d553248621532660539.Vacation-Attraction)
- [Monongahela Incline ](https://www.expedia.ca/Monongahela-Incline-South-Shore.d6078693.Vacation-Attraction)
- [Mount Washington Vacations ](https://www.expedia.ca/Mount-Washington.d6343586.Destination-Travel-Guides)
- [National Aviary ](https://www.expedia.ca/National-Aviary-North-Side.d6078697.Vacation-Attraction)
- [North Side Vacations ](https://www.expedia.ca/North-Side.d6346454.Destination-Travel-Guides)
- [Pnc Park ](https://www.expedia.ca/PNC-Park-North-Shore.d6034814.Vacation-Attraction)
- [Ppg Paints Arena ](https://www.expedia.ca/PPG-Paints-Arena-Downtown-Pittsburgh.d6140367.Vacation-Attraction)
- [Phipps Conservatory ](https://www.expedia.ca/Phipps-Conservatory-Central-Oakland.d6078683.Vacation-Attraction)
- [Visit Bluff ](https://www.expedia.ca/Pittsburgh-Bluff.dx553248634333003951)
- [Visit Downtown Pittsburgh ](https://www.expedia.ca/Pittsburgh-Downtown-Pittsburgh.dx6057662)
- [Visit South Side Flats ](https://www.expedia.ca/Pittsburgh-South-Side-Flats.dx6343589)
- [Visit Terrace Village ](https://www.expedia.ca/Pittsburgh-Terrace-Village.dx804080730279682048)
- [Pittsburgh Vacations ](https://www.expedia.ca/Pittsburgh.d601717.Destination-Travel-Guides)
- [Visit Pittsburgh ](https://www.expedia.ca/Pittsburgh.dx601717)
- [Point State Park ](https://www.expedia.ca/Point-State-Park-Downtown-Pittsburgh.d6078711.Vacation-Attraction)
- [Roberto Clemente Bridge ](https://www.expedia.ca/Roberto-Clemente-Bridge-Pittsburgh.d6078721.Vacation-Attraction)
- [Schenley Park ](https://www.expedia.ca/Schenley-Park-Squirrel-Hill-South.d6078717.Vacation-Attraction)
- [Senator John Heinz Regional History Centre ](https://www.expedia.ca/Senator-John-Heinz-Regional-History-Centre-Downtown-Pittsburgh.d6078699.Vacation-Attraction)
- [Southwest Pennsylvania Vacations ](https://www.expedia.ca/Southwest-Pennsylvania.d6057625.Destination-Travel-Guides)
- [The Waterfront ](https://www.expedia.ca/The-Waterfront-Pittsburgh.d553248621532660523.Vacation-Attraction)
- [Upmc Shadyside ](https://www.expedia.ca/UPMC-Shadyside-Shadyside.d6269693.Vacation-Attraction)
- [University of Pittsburgh ](https://www.expedia.ca/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction)

- [Things to do in Pittsburgh ](https://www.expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)

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