Oakland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,255, price is now CA $1,050 per person
CA $1,050
per person
Aug 6 - Aug 10
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.4/10 Very Good! (100 reviews)
It was a little tricky finding the parking lot but once I was there the apartment was beautiful, well stocked, and very comfortable.

Reviewed on May 12, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,662, price is now CA $1,338 per person
CA $1,338
per person
Aug 6 - Aug 10
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,477, price is now CA $1,192 per person
CA $1,192
per person
Aug 6 - Aug 10
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
9.2/10 Wonderful! (2,011 reviews)
Perfectly located. The rooms are spacious. Beds and linens are comfortable. Appreciate the professionalism of the staff at all the Omni hotels.

Reviewed on May 10, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $1,379, price is now CA $1,150 per person
CA $1,150
per person
Aug 6 - Aug 10
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,066 reviews)
Good central location and friendly staff…

Reviewed on May 12, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,365, price is now CA $1,153 per person
CA $1,153
per person
Aug 6 - Aug 10
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,222 reviews)
Love Pittsburgh, super busy weekend with graduation and the marathon. Walked everywhere, weather was cool but mostly dry. Peddle pusher was a blast! Highly recommend!

Reviewed on May 14, 2026

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh

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 hotels in Downtown Pittsburgh

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from May 26 to May 27
CA $186
CA $212 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (720 reviews)
I have stayed many times to visit my son who attends CMU. This hotel is closest one to the campus that surrounded with good restaurant options. It is about 5 to 10 mins walk to both CMU and Pitts.

Reviewed on May 13, 2026

Courtyard by Marriott Pittsburgh University Center
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
Fully refundable
The price is CA $162 per night from May 25 to May 26
CA $162
CA $185 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
It was an absolutely beautiful hotel. Super friendly staff. I only wish I used the work out room earlier in my stay and not just on the last day, it was super quiet and nice especially to cool off on the patio afterwards.

Reviewed on May 17, 2026

Hotel Indigo Pittsburgh University-Oakland by IHG
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from May 20 to May 21
CA $186
CA $212 total
May 20 - May 21
includes taxes & fees
9.2/10 Wonderful! (984 reviews)
Great breakfast and great location

Reviewed on May 14, 2026

Residence Inn Pittsburgh Oakland/University Place
See all 2,039 properties in Oakland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oakland vacation package cost?
Starting from as low as CA $1,050, a vacation package is your passport to cheaper travel. Custom make your Oakland getaway by selecting from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Oakland?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got everything you need. Choose the combination that suits you and watch your savings stack up. Of course, a package deal is never one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties throughout the world, which lets you customize your Oakland getaway.
Where should I stay in Oakland?
Visitors come from far and wide to see Acrisure Stadium and PNC Park in Oakland. Stay close to these awesome attractions and visit them at your leisure.
What are the top hotels in Oakland?
Get your trip off to an excellent start by booking a stay at Industrial Loft 3 Min To Hillman Cancer Center. It's one of most sought-after hotels in Oakland. Another option is New Huge Spacious 3 Bedroom In Oakland That Over 3000+ Sq Ft.
How far in advance should I book my Oakland vacation?
To bag rock-bottom prices, book ASAP. Airlines usually advertise flight tickets, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Oakland, there are always plenty of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Oakland travel package include?
It all depends on what sort of trip you have in the works. Oakland travel deals can include car rentals, hotels and flights. You can mix and match to find the package that works for you! You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Oakland travel package?
An Expedia travel package can be customized for your circumstances and is a great way to stretch your hard-earned dollars. What you include is totally up to you. Rental cars, hotels and flights — decide on a combination that suits your plans.
Can I choose my airline with an Oakland Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to Oakland in coach or first class, simply select from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Oakland vacation package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Oakland vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your airline, hotel or car rental company may impose a fee. Looking for more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Oakland

University of Pittsburgh in Pittsburgh, PA

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.

University of Pittsburgh
Carnegie Museum of Natural History

Carnegie Museum of Natural History

4.5/5(2 reviews)

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.

Carnegie Museum of Natural History
Carnegie Museum of Art

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.

Carnegie Museum of Art

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $40
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $67
per adult
Whiskey Rebellion & Prohibition Tour
See all activities in Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.