Oakland Vacation Packages

Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,049

per person

Sep 1 - Sep 6

found 17 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.6/10 Excellent! (1,543 reviews)

Great location and room. Staff was great!

Reviewed on Jul 6, 2026

Stay Pittsburgh

Downtown Pittsburgh

CA $1,685

per person

Sep 25 - Sep 28

found 15 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Pittsburgh (PIT)

8/10 Very good! (302 reviews)

Affordable

Reviewed on Jul 4, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $2,175

per person

Sep 25 - Sep 28

found 15 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Pittsburgh (PIT)

8.6/10 Excellent! (1,000 reviews)

It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.

Reviewed on Jun 24, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,056

per person

Sep 1 - Sep 6

found 17 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.6/10 Excellent! (146 reviews)

Great hotel especially for the amenities

Reviewed on Jul 7, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh

CA $1,233

per person

Sep 1 - Sep 6

found 17 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.2/10 Very good! (1,074 reviews)

good location, average and old facility

Reviewed on Jul 1, 2026

Where to stay in Oakland

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

A yellow bridge over a river with a cityscape in the background.

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.

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

100 Lytton Avenue Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $197

CA $225 total

Jul 21 - Jul 22

includes taxes & fees

9/10 Wonderful! (785 reviews)

"Parking is expensive. But if you're a weekend traveler you can park on the street for free."

Reviewed on Jul 6, 2026

The Oaklander Hotel, Autograph Collection

5130 Bigelow Boulevard Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $301

CA $343 total

Aug 2 - Aug 3

includes taxes & fees

9.2/10 Wonderful! (791 reviews)

"I found the property to be excellent in all phases, from cleanliness to staff. A wonderful experience and I will definately stay again when in Pittsburgh."

Reviewed on Jul 1, 2026

Hotel Indigo Pittsburgh University-Oakland by IHG

329 Technology Drive Pittsburgh PA

CA $156

CA $178 total

Aug 2 - Aug 3

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

"Parking was easy and hotel was decently clean could’ve been improved. But staff was super helpful and restaurant/ bar in lobby was amazing."

Reviewed on Jul 6, 2026

See all 2,028 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.

Frequently asked questions

How much does an Oakland vacation package cost?

Starting from as low as CA $1,049, 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.

Stay near popular Oakland attractions

A museum with dinosaur exhibits and a large tree sculpture.

Carnegie Museum of Natural History

9.2/10 (58 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.

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