--- title: "Highland Park Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $934 Expedia" description: "FREE cancellation on select hotels ✅ Bundle Highland Park flight and hotel to build your own Highland Park vacation package & 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Highland Park holiday trips & travel deals." canonical: "https://www.expedia.ca/Highland-Park.d804079224019959808.Destination-Travel-Guides" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-14T08:20:48Z --- # Highland Park Vacation Packages ![A calm lake with a central island, surrounded by a dense forest and a stone bridge.](https://images.trvl-media.com/place/804079224019959808/822031af-c683-41b7-846a-a5968d8c47f7.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 Highland Park 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 - ![An outdoor patio area with a brick wall, outdoor seating, and a grill station.](https://images.trvl-media.com/lodging/5000000/4350000/4342300/4342201/fdf389bf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An indoor swimming pool with a hot tub, lounge chairs, and a safety sign.](https://images.trvl-media.com/lodging/5000000/4350000/4342300/4342201/2423a579.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 6 - Jan 12** ### [Courtyard by Marriott Pittsburgh Washington/Meadow Lands + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-06/2027-01-12/?FromAirport=YVR&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4342201&dealMarker=&paandie=true&cabinClass=e) Washington 6 nights **8.6/10** \- Excellent (1,000 reviews) Roundtrip • Vancouver (YVR) - Pittsburgh (PIT) YVR - PIT • 1 stop PIT - YVR • 1 stop [~~CA $1,142~~](https://www.expedia.ca/) **CA $934** per traveller found 1 day ago - ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/65ee55fd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![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) **Jan 29 - Feb 1** ### [The Westin Pittsburgh, a Marriott Hotel + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14295&dealMarker=&paandie=true&cabinClass=e) Downtown Pittsburgh 3 nights **8.6/10** \- Excellent (1,001 reviews) Roundtrip • Toronto (YYZ) - Pittsburgh (PIT) YYZ - PIT • 1 stop PIT - YYZ • 1 stop [~~CA $1,600~~](https://www.expedia.ca/) **CA $1,247** per traveller found 10 hours ago - ![A modern rooftop lounge with large windows, blue seating, and a city view.](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/w4000h2665x0y2-dfe4b7a7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![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) **Jan 6 - Jan 12** ### [The Oaklander Hotel, Autograph Collection + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-06/2027-01-12/?FromAirport=YVR&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28852483&dealMarker=&paandie=true&cabinClass=e) Oakland 6 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 • Vancouver (YVR) - Pittsburgh (PIT) YVR - PIT • 1 stop PIT - YVR • 1 stop [~~CA $1,570~~](https://www.expedia.ca/) **CA $1,232** per traveller found 1 day ago - ![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) ![A modern living room with a sofa, a coffee table, a dining area with a small table and chairs, and large windows offering city views.](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/53f873e2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 29 - Feb 1** ### [Stay Pittsburgh + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=77861820&dealMarker=&paandie=true&cabinClass=e) Downtown Pittsburgh 3 nights **8.0/10** \- Very good (347 reviews) Roundtrip • Toronto (YYZ) - Pittsburgh (PIT) YYZ - PIT • 1 stop PIT - YYZ • 1 stop [~~CA $1,155~~](https://www.expedia.ca/) **CA $978** per traveller found 10 hours ago - ![A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/5c026a54.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A hotel lobby with a 'Treats' sign, snack shelves, and a welcome sign for Hampton Inn & Suites in Pittsburgh Downtown.](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/151444c3.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 29 - Feb 1** ### [Hampton Inn & Suites Pittsburgh-Downtown + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1668434&dealMarker=&paandie=true&cabinClass=e) Downtown Pittsburgh 3 nights **9.4/10** \- Exceptional (1,368 reviews) "The staff, on the whole, were lovely" Reviewed November 12, 2026 Roundtrip • Toronto (YYZ) - Pittsburgh (PIT) YYZ - PIT • 1 stop PIT - YYZ • 1 stop [~~CA $1,427~~](https://www.expedia.ca/) **CA $1,211** per traveller found 10 hours ago ## Where to stay in Highland Park Find the best Highland Park areas and neighborhoods for the activities you enjoy most. - [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®ionId=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®ionId=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®ionId=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®ionId=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®ionId=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 Highland Park ### Three Rivers Heritage Trail This path winds its way through the center of Pittsburgh and ventures into the leafy suburbs filled with parks and football fields. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532660541) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.