---
title: "Shadyside Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,074 Expedia"
description: "FREE cancellation on select hotels ✅ Bundle Shadyside flight and hotel to build your own Shadyside vacation package & 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Shadyside holiday trips & travel deals."
canonical: "https://www.expedia.ca/Shadyside.d6156339.Destination-Travel-Guides"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-14T20:45:10Z
---

# Shadyside Vacation Packages
![A courtyard with a fountain, brick walls, and trees.](https://images.trvl-media.com/place/6156339/b2f1141a-234f-4e0d-9662-7e5f7d7d28a0.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

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

- ## Plan, book, travel with confidence
- ### Better together
Save up to CA $4,200 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

## The Latest Shadyside Vacation Packages

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

Trip length

3 nights4 nights5 nights6-7 nights

Stars

5 star4 star & up3 star & up2 star & up

Flight class

EconomyPremium economyBusinessFirst class

Remove all filters

- ![A brick building with a large arched entrance labeled "STAYPGH".](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/36fd340f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern living room with large windows, a flat-screen TV, a glass table, a sofa, and a lamp.](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/51dffc7e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 25 - Dec 29**

### [Stay Pittsburgh + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-25/2026-12-29/?FromAirport=YHZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=77861820&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
4 nights

**8.0/10** \- Very good (347 reviews)
Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
YHZ - PIT • 2 stops PIT - YHZ • 1 stop
[~~CA $1,356~~](https://www.expedia.ca/)

**CA $1,074**
per traveller
found 1 day ago
- ![A modern hotel room with a large window, a sofa, and a dining area.](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/f2a32014.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern lobby with a large wooden sculpture, a fireplace, and a seating area.](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/73332914.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 25 - Jan 30**

### [Fairmont Pittsburgh + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-25/2027-01-30/?FromAirport=YHZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3056317&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
5 nights

**8.8/10** \- Excellent (1,002 reviews)
Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
YHZ - PIT • 1 stop PIT - YHZ • 1 stop
[~~CA $1,812~~](https://www.expedia.ca/)

**CA $1,446**
per traveller
found 1 hour ago
- ![A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/52d04c8a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern hotel lobby with a reception desk, a bar area, and a patterned floor.](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/e7c8e126.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 25 - Jan 30**

### [The Oaklander Hotel, Autograph Collection + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-25/2027-01-30/?FromAirport=YHZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28852483&dealMarker=&paandie=true&cabinClass=e)
Oakland
5 nights

**9.2/10** \- Wonderful (860 reviews)
"The room was enormous with huge window, so lots of light. The bathroom was spacious and modern. Good quality bath products in large containers so no wasteful mini bottles There was lots of closet and storage space. There was a coffee bar in the room and plenty of bottled water. Room also had a generous sized desk."
Reviewed November 13, 2026
Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
YHZ - PIT • 1 stop PIT - YHZ • 1 stop
[~~CA $1,679~~](https://www.expedia.ca/)

**CA $1,353**
per traveller
found 1 hour ago
- ![A cityscape with high-rise buildings, including a prominent Westin hotel.](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/65ee55fd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 25 - Jan 30**

### [The Westin Pittsburgh, a Marriott Hotel + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-25/2027-01-30/?FromAirport=YHZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14295&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
5 nights

**8.6/10** \- Excellent (1,002 reviews)
"great"
Reviewed November 14, 2026
Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
YHZ - PIT • 1 stop PIT - YHZ • 1 stop
[~~CA $1,533~~](https://www.expedia.ca/)

**CA $1,265**
per traveller
found 1 hour ago
- ![A modern hotel lobby with a central seating area, large windows, and contemporary furnishings.](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/34b3bae6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![An indoor swimming pool with clear blue water, large windows offering views of a parking lot and greenery, and sun loungers along the poolside.](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/03f8ced0.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 25 - Jan 30**

### [Hyatt Regency Pittsburgh International Airport + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-25/2027-01-30/?FromAirport=YHZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=464013&dealMarker=&paandie=true&cabinClass=e)
Pittsburgh
5 nights

**9.0/10** \- Wonderful (1,807 reviews)
"We stayed one night since we had an early flight. The hotel is clean and has all the amenities but was the loudest hotel we have stayed in. There was noise from the rooms around and above us and from the hallway. We also were woken up at 4am by some loud vibrations within the wall. No one could have slept through the noise. When we brought it to their attention, they apologized but that didn’t help with our sleepless night before a long day of travel. We would stay again only if absolutely..."
Reviewed November 14, 2026
Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
YHZ - PIT • 1 stop PIT - YHZ • 1 stop
[~~CA $1,397~~](https://www.expedia.ca/)

**CA $1,164**
per traveller
found 0 hours ago

## Where to stay in Shadyside

Find the best Shadyside areas and neighborhoods for the activities you enjoy most. [Learn more about Shadyside](https://www.expedia.ca/Pittsburgh-Shadyside.dx6156339)

- [Downtown Pittsburgh](#)
- [North Shore](#)
- [Oakland](#)
- [Strip District](#)
- [North Side](#)

![A yellow bridge over a river with a cityscape in the background.](https://images.trvl-media.com/place/6057662/7df71e93-fe04-46c9-a8b8-caf07e34fbb5.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Downtown Pittsburgh](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6057662)

### Downtown Pittsburgh

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.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6057662)

![A city skyline at dusk with illuminated buildings, a prominent bridge, and a river.](https://images.trvl-media.com/place/553248633938969308/308a169b-6070-4d33-8240-3c8c56c3b52a.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

Photo by TM

[View properties in map for North Shore](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248633938969308)

### North Shore

Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248633938969308)

![A dinosaur statue in front of a historic building with inscriptions.](https://images.trvl-media.com/place/183908/02f384e3-74f3-4d88-9c41-fb1cf0293ad6.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Oakland](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=183908)

### Oakland

Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=183908)

![A building with a large sign reading 'THE TERMINAL' and storefronts for 'posman books' and 'solidcore.'](https://images.trvl-media.com/place/6343592/0ef3f539-1279-419d-a82e-f7983d5316e2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

Photo by TM

[View properties in map for Strip District](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6343592)

### Strip District

Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6343592)

![A bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.](https://images.trvl-media.com/place/891415173200363520/ec08a67b-851f-44eb-939a-c02f52473c02.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for North Side](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=891415173200363520)

### North Side

If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=891415173200363520)

## Discover the most popular places to visit in Shadyside

### Walnut Street

During your trip to Pittsburgh, you can find the perfect gifts to bring home at Walnut Street. Savor the area's restaurants and bars.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248633862333415)

### Mellon Park Tennis Center

Catch an event at Mellon Park Tennis Center during your trip to Pittsburgh. Visit the area's shops, or simply enjoy its restaurants.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=941624853971271680)

### What to do near Shadyside

![Picture 3 for Activity Pittsburgh: Museum of Illusions Entrance Ticket](https://mediaim.expedia.com/localexpert/50578729/8a154cb3-982d-4775-90d1-efbf077701e6.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Pittsburgh: Museum of Illusions Entrance Ticket](https://www.expedia.ca/things-to-do/a.a50578729.activity-details?rid=6156339)

CA $41

per adult

86% of travellers recommend

![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/01f6f0c7-8f7b-4459-af50-26971080b4b2.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://www.expedia.ca/things-to-do/a.a697587.activity-details?rid=6156339)

CA $19

per adult

0% of travellers recommend

![Pittsburgh: Pasta Making Class With Local Chef](https://mediaim.expedia.com/localexpert/51792538/fad517f0-9b5f-4f79-97fb-6db03bbbc76e.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Pittsburgh: Pasta Making Class With Local Chef](https://www.expedia.ca/things-to-do/a.a51792538.activity-details?rid=6156339)

CA $105

per adult

0% of travellers recommend

[See all activities near Shadyside](https://www.expedia.ca/things-to-do/search?rid=6156339)

## Shadyside Hotel Deals

### [Mansions on Fifth Hotel](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information)

![A large stone building with a central entrance, multiple windows, and a symmetrical facade.](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/2df82a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 5105 Fifth Avenue, Pittsburgh, PA, 15232, US
- Location: Shadyside
- Star rating: 4/5
- Guest rating: 9/10 (Wonderful, 1011 reviews)
- Price: CA $204, CA $233 total, includes taxes & fees, Dec 9 - Dec 10

### [The Inn on Negley](https://www.expedia.ca/Pittsburgh-Hotels-The-Inn-On-Negley.h1154383.Hotel-Information)

![A white building with a porch, a sign for The Inn on Negley, and a brick staircase leading up to the entrance.](https://images.trvl-media.com/lodging/2000000/1160000/1154400/1154383/3d117d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 703 South Negley Avenue, Pittsburgh, PA, 15232, US
- Location: Shadyside
- Star rating: 4/5
- Guest rating: 10/10 (Exceptional, 230 reviews)
- Price: CA $470, CA $535 total, includes taxes & fees, Dec 2 - Dec 3
- Review: The breakfast was absolutely delicious! The neighbourhood beautiful. The Inn was so nice and quiet. The bath was deep and oh so NICE!

### [Hyatt House Pittsburgh/Bloomfield/Shadyside](https://www.expedia.ca/Pittsburgh-Hotels-Hyatt-House-PittsburghBloomfieldShadyside.h9707925.Hotel-Information)

![An outdoor seating area with a stone fire pit, cushioned sofas, and a table with chairs.](https://images.trvl-media.com/lodging/10000000/9710000/9708000/9707925/f987c707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 5335 Baum Blvd, Pittsburgh, PA, 15224, US
- Location: Bloomfield, 0.6 km from Shadyside
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 1021 reviews)
- Price: CA $169, CA $192 total, includes taxes & fees, Dec 13 - Dec 14

### [The Maverick by Kasa](https://www.expedia.ca/Pittsburgh-Hotels-The-Maverick-By-Kasa.h71086666.Hotel-Information)

![A double door with a stone frame and a decorative arch above it.](https://images.trvl-media.com/lodging/72000000/71090000/71086700/71086666/208f1544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 120 S Whitfield St, Pittsburgh, PA, 15206, US
- Location: East Liberty, 1.4 km from Shadyside
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 1001 reviews)
- Price: CA $128, CA $146 total, includes taxes & fees, Nov 23 - Nov 24

### [Hotel Indigo Pittsburgh East Liberty by IHG](https://www.expedia.ca/Pittsburgh-Hotels-Hotel-Indigo-Pittsburgh-East-Liberty.h9032700.Hotel-Information)

![A restaurant with multiple dining tables and chairs, large windows offering a view of the street, and a modern interior design.](https://images.trvl-media.com/lodging/10000000/9040000/9032700/9032700/ac8ade38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 123 North Highland Avenue, Pittsburgh, PA, 15206, US
- Location: East Liberty, 1.6 km from Shadyside
- Star rating: 3.5/5
- Guest rating: 8/10 (Very good, 1003 reviews)
- Price: CA $136, CA $155 total, includes taxes & fees, Nov 23 - Nov 24
- Review: The staffs were great but the cleaning crew ain’t doing a good job. Found hair and dead flies on the bed, floor and the table.

### [Courtyard by Marriott Pittsburgh University Center](https://www.expedia.ca/Pittsburgh-Hotels-Wyndham-Pittsburgh-University-Center.h3215.Hotel-Information)

![A bar area with a wooden backdrop, a glass display case with bottles, and four black bar stools.](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/8b478daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 100 Lytton Avenue, Pittsburgh, PA, 15213, US
- Location: 1.6 km from Shadyside
- Star rating: 3.5/5
- Guest rating: 9/10 (Wonderful, 984 reviews)
- Price: CA $149, CA $170 total, includes taxes & fees, Nov 23 - Nov 24
- Review: In addition to the on-site amenities, this hotel is conveniently located in Pittsburgh's Oakland neighborhood, walking distance from University of Pittsburgh's Cathedral of Learning and also the Carnegie Museums.

### [SpringHill Suites by Marriott Pittsburgh Bakery Square](https://www.expedia.ca/Pittsburgh-Hotels-SpringHill-Suites-By-Marriott-Pittsburgh-Bakery-Square.h3493342.Hotel-Information)

![A rooftop lounge with a stone fire pit, cushioned seating, and a view of the cityscape.](https://images.trvl-media.com/lodging/4000000/3500000/3493400/3493342/603eb9aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 134 Bakery Square Blvd, Pittsburgh, PA, 15206, US
- Location: 1.9 km from Shadyside
- Star rating: 3/5
- Guest rating: 8.8/10 (Excellent, 1000 reviews)
- Price: CA $156, CA $178 total, includes taxes & fees, Nov 22 - Nov 23

### [Hilton Garden Inn Pittsburgh University Place](https://www.expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-University-Place.h118998.Hotel-Information)

![The exterior of the Hilton Garden Inn with a prominent illuminated sign, a large entrance with glass doors, and an American flag displayed outside.](https://images.trvl-media.com/lodging/1000000/120000/119000/118998/6c759b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 3454 Forbes Ave, Pittsburgh, PA, 15213, US
- Location: 2.4 km from Shadyside
- Star rating: 3/5
- Guest rating: 8.8/10 (Excellent, 1030 reviews)
- Price: CA $181, CA $206 total, includes taxes & fees, Nov 23 - Nov 24

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.

[See all properties in Shadyside](https://www.expedia.ca/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&regionId=6156339&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Frequently Asked Questions

### How much does a Shadyside vacation package cost?

From just CA $1,074\. Yes, you read that correctly. Our Shadyside vacation packages are the quickest way to make your dollars go much further. Combine your favorite hotels, flights and car rentals and explore this lively destination.

### How do I get a cheap travel package to Shadyside?

Booking a Shadyside vacation package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1,000,000 hotels across the globe. With such a broad range to pick from, you'll have no hassles creating your ideal escape.

### Where should I stay in Shadyside?

Make sightseeing a breeze by staying someplace just a stone's throw away from Shadyside's biggest attractions. Acrisure Stadium and PNC Park are two traveler favorites.

### What are the top hotels in Shadyside?

If it's your very first time in Shadyside, reserve a room at [The Inn On Negley](https://www.expedia.ca/Pittsburgh-Hotels-The-Inn-On-Negley.h1154383.Hotel-Information) or [Mansions on Fifth Hotel](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information). Both hotels offer friendly service and are favorites among many savvy travelers.

### How far in advance should I book my Shadyside vacation?

It can be tricky to know exactly when the best time is to book your Shadyside vacation. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to a year before departure. If you're eager to escape on a last-minute getaway, no need to worry! There are terrific bargains advertised on Expedia every day.

### What does an Expedia Shadyside travel package include?

Flights, car rentals and hotels — we connect you to the best deals. All you'll have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to put together an unforgettable Shadyside trip.

### What should I know before booking a Shadyside travel package?

You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome vacation is only a few clicks away.

### Can I choose my airline with a Shadyside Expedia vacation package?

Yes, you're in charge. We offer more than 550 airlines worldwide, so you can tailor your Shadyside escape according to your travel preferences.

### If I'm not able to travel, can I cancel my Shadyside vacation package?

We totally get that life can throw you the odd curveball. If you've booked a Shadyside vacation package and have to cancel or amend it, we can help. We suggest having a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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