Title: Oakland Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,219 Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Pittsburgh-Hotels.0-n183908-0.Travel-Guide-Filter-Hotels)[Flights to Pittsburgh](https://expedia.ca/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights)[Things to do in Pittsburgh](https://expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d183908.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183908/443b7585-02de-4d96-b9dc-a7bbd20b134f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland 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 Holiday Package Deals in Oakland Price found within the past 48 hours. Click for updated prices. ![Hilton Garden Inn Pittsburgh Airport](https://images.trvl-media.com/lodging/19000000/18570000/18566700/18566645/5c90a591_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Pittsburgh Airport CA $1,219 per person Jun 5 - Jun 10 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Pittsburgh (PIT) 9/10 Wonderful! (1,004 reviews) Luv this place will stay again when we go away!! Reviewed on Mar 27, 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 $1,656 per person Jun 16 - Jun 23 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Pittsburgh (PIT) 8.2/10 Very Good! (71 reviews) Amazing kitchen,trash chute is fantastic. The staff were the best Room was so clean. Proximity to everything is perfect. Reviewed on Mar 30, 2026 ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/b0ce2278_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Pittsburgh Downtown Downtown Pittsburgh CA $1,311 per person Jun 16 - Jun 23 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Pittsburgh (PIT) 8.2/10 Very Good! (3,437 reviews) Yes breakfast was amazing Reviewed on Mar 30, 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 $1,919 per person Jun 16 - Jun 23 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Pittsburgh (PIT) 8.6/10 Excellent! (1,001 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 ![The Colonial Mt. Lebanon by Luxe PGH](https://images.trvl-media.com/lodging/110000000/109860000/109852700/109852698/4cbe0c70_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonial Mt. Lebanon by Luxe PGH Mount Lebanon CA $2,016 per person Jun 5 - Jun 10 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Pittsburgh (PIT) 2/10 (2 reviews) ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. [Learn more about Oakland](https://expedia.ca/Pittsburgh-Oakland.dx183908) ![Downtown Pittsburgh](https://images.trvl-media.com/place/6057662/7df71e93-fe04-46c9-a8b8-caf07e34fbb5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Pittsburgh 2 out of top 10 points of interest in this area 4.5/5(190 area reviews) 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. [Find hotel + flight trips in Downtown Pittsburgh](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Pittsburgh&DestID=6057662&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![North Shore](https://images.trvl-media.com/place/553248633938969308/c1d2f3a4-eff8-47ed-b1af-f88f96028a9d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North Shore 2 out of top 10 points of interest in this area 4.5/5(30 area reviews) 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. [Find hotel + flight trips in North Shore](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20Shore&DestID=553248633938969308&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![View of the Strip District, from Frank Curto Park in Pittsburgh, Pennsylvania](https://images.trvl-media.com/place/6343592/dc99580f-c44b-45af-9529-30dbfbc703a3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Strip District 4/5(1 area review) 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. [Find hotel + flight trips in Strip District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Strip%20District&DestID=6343592&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![PITTSBURGH, PENNSYLVANIA, USA 4-30-2018 Mellon Park. Designed in 1929 and later donated to the city by Richard Mellon as part of his estate in the Shadyside neighborhood of the the City](https://images.trvl-media.com/place/6156339/b2f1141a-234f-4e0d-9662-7e5f7d7d28a0.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shadyside Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible. [Find hotel + flight trips in Shadyside](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Shadyside&DestID=6156339&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Mount Washington](https://images.trvl-media.com/place/553248634333002587/46d6c5fe-6780-4437-8b35-94be38c886fb.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Mount Washington Consider a visit to Ohio River Valley and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station. [Find hotel + flight trips in Mount Washington](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Mount%20Washington&DestID=6343586&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Oakland Hotel Deals ![Courtyard by Marriott Pittsburgh University Center](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/8b478daa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Pittsburgh University Center 100 Lytton Avenue Pittsburgh PA Fully refundableReserve now, pay when you stay CA $188 CA $214 total Apr 26 - Apr 27 includes taxes & fees 9/10 Wonderful! (654 reviews) Everything was wonderful! Getting checked in was a little numb, but Wayne went above and beyond in his effort to take care of it. Our rooms were perfect! The staff was attentive and friendly. The bartender at the evening reception was excellent! The food was fresh and very delicious! The hot tub ... Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=3215&PinnedHotelID=3215&HadPinnedHotel=true®ionId=183908) ![Hotel Indigo Pittsburgh University-Oakland by IHG](https://images.trvl-media.com/lodging/20000000/19910000/19901600/19901526/6dac0c0b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Indigo Pittsburgh University-Oakland by IHG 329 Technology Drive Pittsburgh PA CA $177 CA $202 total Apr 5 - Apr 6 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) Stayed one night for pleasure. Property abuts a busy road near the highway. Would recommend NOT staying on that side of hotel as it is noisy all night long. Shower drain was 95% clogged. I won't be staying here again. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=19901526&PinnedHotelID=19901526&HadPinnedHotel=true®ionId=183908) ![The Oaklander Hotel, Autograph Collection](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/52d04c8a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Oaklander Hotel, Autograph Collection 5130 Bigelow Boulevard Pittsburgh PA Fully refundableReserve now, pay when you stay CA $347 CA $395 total Apr 5 - Apr 6 includes taxes & fees 9.2/10 Wonderful! (753 reviews) very nice. Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=28852483&PinnedHotelID=28852483&HadPinnedHotel=true®ionId=183908) [See all 1,971 properties in Oakland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026®ionId=183908) 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) ## Frequently asked questions ### How much does an Oakland vacation package cost? ### How do I get a cheap travel package to Oakland? ### Where should I stay in Oakland? ### What are the top hotels in Oakland? ### How far in advance should I book my Oakland vacation? ### What does an Expedia Oakland travel package include? ### What should I know before booking an Oakland travel package? ### Can I choose my airline with an Oakland Expedia vacation package? ### If I'm not able to travel, can I cancel my Oakland vacation package? ### Discover the most popular places to visit in Oakland ![University of Pittsburgh in Pittsburgh, PA ](https://images.trvl-media.com/place/6090505/783a779d-9b7b-411b-8978-ebc0679a7952.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Pittsburgh 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) ![Carnegie Museum of Natural History](https://images.trvl-media.com/place/6078701/3465d6b7-2fa2-461f-8376-102e6e82bbe2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Carnegie Museum of Natural History From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums. [](https://expedia.ca/Carnegie-Museum-Of-Natural-History-Oakland.d6078701.Vacation-Attraction) ![Carnegie Museum of Art](https://images.trvl-media.com/place/6078685/733a42fe-96c3-439b-b965-506fbb2da522.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Carnegie Museum of Art If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries. [](https://expedia.ca/Carnegie-Museum-Of-Art-Oakland.d6078685.Vacation-Attraction) ### Things to do ![Pittsburgh: Museum of Illusions Entrance Ticket](https://mediaim.expedia.com/localexpert/50578729/7320642b-dd30-4e80-8314-21019365b5d8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh: Museum of Illusions Entrance Ticket CA $40 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/pittsburgh-museum-of-illusions-entrance-ticket.a50578729.activity-details) ![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/01f6f0c7-8f7b-4459-af50-26971080b4b2.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 $67 per adult [](https://expedia.ca/things-to-do/whiskey-rebellion-prohibition-tour.a1359320.activity-details) [See all activities in Pittsburgh](https://expedia.ca/things-to-do/search?rid=183908) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.