Oakland Vacation Packages

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Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,429, price is now CA $1,015 per person
CA $1,015
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Great price so close to Acrisure for a football game. Clean and well taken care of

Reviewed on Aug. 21, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,124, price is now CA $1,436 per person
CA $1,436
per person
Oct 11 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (12 reviews)
The people at the service desk were fine. Some were helpful and some were not.

Reviewed on Aug. 19, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was CA $1,852, price is now CA $1,302 per person
CA $1,302
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Good location, friendly staff, spacious bathroom.

Reviewed on Aug. 18, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $2,000, price is now CA $1,430 per person
CA $1,430
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
The property was great the and the sfaff were awesome.

Reviewed on Aug. 17, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $2,731, price is now CA $2,023 per person
CA $2,023
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Everything was great

Reviewed on Aug. 12, 2025

Where to stay in Oakland

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

2 out of top 10 points of interest in this area
4.5/5(187 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 $180 per night from Aug 26 to Aug 27
CA $180
CA $205 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (407 reviews)
"Very nice staff & a nice room"

Reviewed on Aug. 18, 2025

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 $169 per night from Aug 31 to Sep 1
CA $169
CA $193 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great room, terrific bar staff, convenient to University. We had a great time!"

Reviewed on Aug. 10, 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Aug 28 to Aug 29
CA $272
CA $310 total
Aug 28 - Aug 29
includes taxes & fees
9.2/10 Wonderful! (677 reviews)
"I travel quite a bit but this one really impressed me!"

Reviewed on Aug. 16, 2025

The Oaklander Hotel, Autograph Collection
See all 1,753 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 $1,015, 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

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 featuring views and interior views

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 which includes interior views, a statue or sculpture and 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, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

CA $43
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $186
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

CA $76
per adult
Pittsburgh Pirates Baseball Game at PNC Park
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.