Oakland Vacation Packages 2025/2026 from $240

Oakland flight + hotel vacation packages

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

DoubleTree by Hilton Pittsburgh - Green Tree

$240

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Pittsburgh (PIT)

This hotel features a restaurant, a gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, a 24-hour business center, and a coffee shop are also offered.

Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

$263

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a computer station, and luggage storage are also on offer.

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

$245

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Pittsburgh (PIT)

The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Hilton Garden Inn Pittsburgh Airport

$271

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Pittsburgh (PIT)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

$271

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. A terrace, a snack bar/deli, and luggage storage are also on offer.

Top Oakland hotels deals

Courtyard by Marriott Pittsburgh University Center

100 Lytton Avenue, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$158 total

Sep 4 - Sep 5

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. Self parking, express check-out, and dry cleaning are also offered.

Pool

Free WiFi

Hotel Indigo Pittsburgh University-Oakland by IHG

329 Technology Drive, Pittsburgh, PA

Free Cancellation

$127 nightly

$145 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the a rooftop terrace and perks like a free area shuttle.

Pet friendly

Free WiFi

The Oaklander Hotel, Autograph Collection

5130 Bigelow Boulevard, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$214 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.

Pet friendly

Free WiFi

Residence Inn Pittsburgh Oakland/University Place

3341 Forbes Ave, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$170 total

Sep 4 - Sep 5

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a complimentary grocery shopping service are also provided.

Pool

Breakfast included

Hampton Inn Pittsburgh University/Medical Center

3315 Hamlet Street, Pittsburgh, PA

Get rates

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and concierge services.

Breakfast included

Pet friendly

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$172 total

Sep 28 - Sep 29

Total with taxes and fees

The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Pool

Pet friendly

Don't see what you're looking for?

See all available properties in Oakland

View all properties

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.

Popular places to visit

University of Pittsburgh

4.5/5(843 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.

Carnegie Museum of Natural History

4.5/5(48 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 Art

5/5(4 reviews)

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.

Frequently asked questions

How much are vacation packages to Oakland?

With vacation packages being sold for just $240, it's not necessary to drain your bank balance for your trip to Oakland. Travelocity can help. Combine flights, hotels and experiences into a package and land fantastic discounts. The more you book, the more you save.

Where can I get the best vacation package deals for Oakland?

Travelocity is here to help you snap up a great Oakland package deal. With more than 400 airlines and 1,000,000 properties around the world, you're bound to be able to put together the perfect itinerary.

Why should I book my Oakland vacation package via Travelocity?

We offer 24/7 customer support, top-quality service and a Price Match Guarantee. Life's a great big journey — and we have exciting destinations for you to journey to all over the world. Roam with us and make your hip pocket happy.

Will I save money on my Oakland car rental if I bundle it with a hotel or flight?

Definitely — and if you also add an experience or activity to your Oakland vacation package, you'll pick up even more savings. With a package, you can find things to do in the region that are perfect for you, Then, hop in your rental car and work your way through the list. Geneva State Park is one awesome attraction to put on your itinerary. You'll find it 110 mi from Oakland.

What is there to do in Oakland?

Take out your vacation itinerary and make a note of Carnegie Museum of Natural History and Petersen Events Center. They're some of the most popular attractions in Oakland.