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
0.5 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 ...
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. ...
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

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

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
1.37 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 ...
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place Pittsburgh PA
3.16 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 ...
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 ...
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
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

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 ...
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 ...
Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
250 Forbes Avenue Pittsburgh PA
3.58 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 ...
TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
177 40th Street Pittsburgh PA
2.9 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
5335 Baum Blvd Pittsburgh PA
2.27 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 ...
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
123 North Highland Avenue Pittsburgh PA
3.6 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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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.

Delta
Thu, Jun 4 - Mon, Jun 8
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$141 Roundtrip, found 23 hours ago
$141
Roundtrip
found 23 hours ago
Select Delta flight, departing Thu, Jun 4 from John F. Kennedy Intl. to Pittsburgh Intl., returning Mon, Jun 8, priced at $141 found 23 hours ago
Spirit Airlines
Fri, Jan 30 - Tue, Feb 3
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$168 Roundtrip, found 16 hours ago
$168
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Fri, Jan 30 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Tue, Feb 3, priced at $168 found 16 hours ago
JetBlue Airways
Fri, Jun 5 - Tue, Jun 9
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$177 Roundtrip, found 23 hours ago
$177
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Jun 5 from John F. Kennedy Intl. to Pittsburgh Intl., returning Tue, Jun 9, priced at $177 found 23 hours ago
American Airlines
Sun, Jun 7 - Thu, Jun 11
LGA
LaGuardia
PIT
Pittsburgh Intl.
$190 Roundtrip, found 23 hours ago
$190
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sun, Jun 7 from LaGuardia to Pittsburgh Intl., returning Thu, Jun 11, priced at $190 found 23 hours ago
Frontier Airlines
Mon, Jan 26 - Mon, Feb 2
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$191 Roundtrip, found 16 hours ago
$191
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Mon, Jan 26 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Mon, Feb 2, priced at $191 found 16 hours ago