Oakland Vacation Packages for 2026
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.
SpringHill Suites by Marriott Pittsburgh Washington
Price was $608, price is now $499 per person
$499
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this business-friendly 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 F. Julius LeMoyne House are located nearby.
Stay Pittsburgh
Downtown Pittsburgh
Price was $1,104, price is now $845 per person
$845
per person
Jun 20 - Jun 27
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Pittsburgh (PIT)
Stay at this aparthotel in Pittsburgh. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Fairmont Pittsburgh
Downtown Pittsburgh
Save 100% on your flight
Price was $1,784, price is now $1,398 per person
$1,398
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this luxury hotel in Pittsburgh. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and PPG Paints Arena are located nearby.
Crowne Plaza Suites Pittsburgh South by IHG
Price was $701, price is now $575 per person
$575
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Bethel Park. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions South Hills Village and Montour Trail are located nearby.
Hotel Indigo Pittsburgh University-Oakland by IHG
Oakland
Price was $1,012, price is now $841 per person
$841
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was $921, price is now $766 per person
$766
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
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 the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Top Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
0.5 km from Oakland
Stay at this hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
1.37 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
0.61 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 breakfast and the helpful ...
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
0.38 km from Oakland
Book a stay at this luxury hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
4.02 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 ...
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
5.27 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Acrisure Stadium and PNC Park ...
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
3.16 km from Oakland
Book a stay at this luxury hotel in Pittsburgh. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Hyatt Regency Pittsburgh International Airport
710 Aviation Avenue Pittsburgh PA
26.08 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
2.8 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Joinery Hotel Pittsburgh, Curio Collection by Hilton
453 Boulevard of the Allies Pittsburgh PA
3.39 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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 ...
Drury Plaza Hotel Pittsburgh Downtown
745 Grant Street Pittsburgh PA
3.01 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
8.91 km from Oakland
Stay at this 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 in ...
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.
Wed, Jun 3 - Wed, Jun 10
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Wed, Jun 3 - Wed, Jun 10
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Wed, Jun 3 - Wed, Jun 10
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$207 Roundtrip, found 2 hours ago
$207
Roundtrip
found 2 hours ago
Wed, Jun 3 - Wed, Jun 10
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Tue, Jun 30 - Wed, Jul 8
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago