Oakland Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Oakland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE INN- PITTSBURGH
Banksville
Price was $415, price is now $287 per person
$287
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this 3-star inn in Pittsburgh. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Acrisure Stadium and PNC Park are located nearby.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Save 100% on your flight
Price was $629, price is now $394 per person
$394
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Save 100% on your flight
Price was $869, price is now $573 per person
$573
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.
Hilton Garden Inn Pittsburgh Airport
Save 100% on your flight
Price was $772, price is now $536 per person
$536
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this 3-star business-friendly hotel in Coraopolis. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Mall at Robinson and UPMC Events Center are located nearby.
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Save 100% on your flight
Price was $931, price is now $653 per person
$653
per person
Nov 1 - Nov 6
found 10 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this 4-star apartment in Pittsburgh. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions PPG Paints Arena and PNC Park are located nearby.
Hampton Inn & Suites Pittsburgh-Meadow Lands
Price was $554, price is now $389 per person
$389
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Pittsburgh (PIT)
Stay at this hotel in Washington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Casino at the Meadows and Tanger Outlet Center are located nearby.
Top Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
0.46 km from Oakland
Stay at this 3.5-star hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
1.4 km from Oakland
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard, Pittsburgh, PA
0.38 km from Oakland
Stay at this 4.5-star luxury hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave, Pittsburgh, PA
0.61 km from Oakland
Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Hampton Inn Pittsburgh University/Medical Center
3315 Hamlet Street, Pittsburgh, PA
0.9 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the ...
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl, Pittsburgh, PA
4.02 km from Oakland
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff ...
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
One Bigelow Square, Pittsburgh, PA
2.98 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Joinery Hotel Pittsburgh, Curio Collection by Hilton
453 Boulevard of the Allies, Pittsburgh, PA
3.39 km from Oakland
Stay at this 4-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Omni William Penn Hotel
530 William Penn Place, Pittsburgh, PA
3.19 km from Oakland
Book a stay at this historic hotel in Pittsburgh. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn by Wyndham Pittsburgh Airport
8507 University Blvd, Coraopolis, PA
23.41 km from Oakland
Stay at this 3-star family-friendly hotel in Coraopolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Wyndham Garden Pittsburgh Airport
1 Industry Lane, Pittsburgh, PA
20.42 km from Oakland
Stay at this 3-star hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue, Pittsburgh, PA
8.84 km from Oakland
Stay at this 4-star hotel in Pittsburgh. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG
875 Greentree Road, Pittsburgh, PA
7.12 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 23 - Thu, Oct 30
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$76 Roundtrip, found 5 days ago
$76
Roundtrip
found 5 days ago
Mon, Oct 27 - Sat, Nov 1
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Tue, Oct 28 - Wed, Oct 29
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 5 days ago
$121
Roundtrip
found 5 days ago
Sun, Oct 5 - Mon, Oct 6
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$122 Roundtrip, found 6 days ago
$122
Roundtrip
found 6 days ago
Thu, Oct 2 - Wed, Oct 8
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$122 Roundtrip, found 6 days ago
$122
Roundtrip
found 6 days ago