Oakland Vacation Packages

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Top Holiday Package Deals in Oakland

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

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,060, price is now CA $925 per person
CA $925
per person
Apr 3 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
Clean and very cozy

Reviewed on Feb 1, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,601, price is now CA $1,355 per person
CA $1,355
per person
Apr 3 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 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

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Price was CA $1,598, price is now CA $1,381 per person
CA $1,381
per person
Apr 3 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,318 reviews)
Convenient location and easy check in.

Reviewed on Feb 11, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,313, price is now CA $1,135 per person
CA $1,135
per person
Apr 3 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Very friendly staff and clean room.

Reviewed on Feb 1, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,113, price is now CA $993 per person
CA $993
per person
Apr 3 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8/10 Very Good! (1,009 reviews)
Service at the front are pretty nice and helpful as well as the servers in the restaurant.

Reviewed on Feb 8, 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 which includes a bridge and a river or creek

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 $155 per night from Feb 23 to Feb 24
CA $155
CA $176 total
Feb 23 - Feb 24
includes taxes & fees
9/10 Wonderful! (602 reviews)
Convenient location. Great price

Reviewed on Feb 9, 2026

Courtyard by Marriott Pittsburgh University Center
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 $264 per night from Mar 12 to Mar 13
CA $264
CA $301 total
Mar 12 - Mar 13
includes taxes & fees
9.2/10 Wonderful! (741 reviews)
Friendly folks at the front desk. Kayla the bartender was awesome! The room was stocked with top notch products and amenities. Wish we could have stayed one more night, as it was so comfortable and welcoming.

Reviewed on Feb 2, 2026

The Oaklander Hotel, Autograph Collection
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 $160 per night from Feb 23 to Feb 24
CA $160
CA $182 total
Feb 23 - Feb 24
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Great

Reviewed on Feb 7, 2026

Hotel Indigo Pittsburgh University-Oakland by IHG
See all 1,908 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 $925, 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 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 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
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $80
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike 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.