Oakland Vacation Packages

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Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
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)
Highly recommend!! Rooms and bathrooms are HUGE!!

Reviewed on Aug. 3, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on Jun. 22, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.6/10 Good! (12 reviews)
Practical and accessible

Reviewed on Jul. 12, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Great location……clean and friendly staff…loved the valet parking!!

Reviewed on Aug. 8, 2025

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.8/10 Good! (160 reviews)
Clean and good location

Reviewed on Aug. 6, 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
The price is CA $179 per night from Aug 24 to Aug 25
CA $179
CA $204 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (398 reviews)
"Very convenient to UPitt and Carnegie Mellon"

Reviewed on Aug. 3, 2025

Courtyard by Marriott Pittsburgh University Center
Hampton Inn Pittsburgh University/Medical Center

Hampton Inn Pittsburgh University/Medical Center

2.5 out of 5
3315 Hamlet Street, Pittsburgh, PA
8/10 Very Good! (1,056 reviews)
"Great property!"

Reviewed on Jul. 29, 2025

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Hampton Inn Pittsburgh University/Medical 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 Sep 1 to Sep 2
CA $169
CA $193 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Excellent food and service. The only problem was a car alarm that went off continuously starting at 2:00am in the hotel parking lot. I walked down to the parking lot personally and reported the specific car and license plate to the front desk. The alarm continued continued to go off throughout the ..."

Reviewed on Aug. 5, 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
See all 1,757 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
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Frequently asked questions

How much does an Oakland vacation package cost?
Starting from as low as CA $991, 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

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

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 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
Pittsburgh: Golden Triangle Guided Walking Tour at Sunset

Pittsburgh: Golden Triangle Guided Walking Tour at Sunset

CA $38
per adult
Pittsburgh: Golden Triangle Guided Walking Tour at Sunset
Step into the shadows and discover the haunting tales of our city's past.

Pittsburgh Ghosts Steel City Haunted Tour

CA $36
per adult
100% of travellers recommend
Pittsburgh Ghosts Steel City Haunted 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.