Oakland Vacation Packages for 2026

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Top Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
0.46 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 ...
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
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. ...
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
1.4 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 ...
Hampton Inn Pittsburgh University/Medical Center

Hampton Inn Pittsburgh University/Medical Center

2.5 out of 5
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

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
4.02 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
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 ...
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
2.72 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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
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 ...
Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
250 Forbes Avenue Pittsburgh PA
3.57 km from Oakland
Stay at this hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a free casino shuttle. Our guests praise the helpful staff and the clean rooms ...
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
620 William Penn Place Pittsburgh PA
3.13 km from Oakland
Book a stay at this luxury hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Sheraton Pittsburgh Hotel at Station Square

Sheraton Pittsburgh Hotel at Station Square

3.5 out of 5
300 West Station Square Drive Pittsburgh PA
4.09 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
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 room service. Our guests praise the restaurant and the ...
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
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 ...
Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
510 Market Street Pittsburgh PA
3.55 km from Oakland
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 ...
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
8.84 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 ...
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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.

Spirit Airlines
Mon, Jan 12 - Wed, Jan 28
DFW
Dallas-Fort Worth Intl.
PIT
Pittsburgh Intl.
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jan 12 from Dallas-Fort Worth Intl. to Pittsburgh Intl., returning Wed, Jan 28, priced at $110 found 5 days ago
Frontier Airlines
Mon, Feb 2 - Sat, Feb 14
DFW
Dallas-Fort Worth Intl.
PIT
Pittsburgh Intl.
$192 Roundtrip, found 5 days ago
$192
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Feb 2 from Dallas-Fort Worth Intl. to Pittsburgh Intl., returning Sat, Feb 14, priced at $192 found 5 days ago
Delta
Tue, Feb 24 - Tue, Mar 10
DAL
Love Field
PIT
Pittsburgh Intl.
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 24 from Love Field to Pittsburgh Intl., returning Tue, Mar 10, priced at $227 found 5 days ago
Southwest Airlines
Thu, Jan 8 - Wed, Jan 14
DAL
Love Field
PIT
Pittsburgh Intl.
$262 Roundtrip, found 6 days ago
$262
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jan 8 from Love Field to Pittsburgh Intl., returning Wed, Jan 14, priced at $262 found 6 days ago
JetBlue Airways
Wed, Mar 25 - Sat, Mar 28
LAX
Los Angeles Intl.
PIT
Pittsburgh Intl.
$301 Roundtrip, found 5 days ago
$301
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Los Angeles Intl. to Pittsburgh Intl., returning Sat, Mar 28, priced at $301 found 5 days ago