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Oakland Vacation Packages

3-4 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 15 - Sep 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 15 - Sep 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 15 - Sep 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)

Cheap Hotel Deals in Oakland

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
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 ...
Courtyard by Marriott Pittsburgh University Center
Hampton Inn Pittsburgh University/Medical Center

Hampton Inn Pittsburgh University/Medical Center

2.5 out of 5
3315 Hamlet Street, Pittsburgh, PA
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 ...
Hampton Inn Pittsburgh University/Medical Center
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive, Pittsburgh, PA
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 ...
Hotel Indigo Pittsburgh University-Oakland by IHG
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The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
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. ...
The Oaklander Hotel, Autograph Collection
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
3341 Forbes Ave, Pittsburgh, PA
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 ...
Residence Inn Pittsburgh Oakland/University Place
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
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 ...
Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
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 ...
Omni William Penn Hotel
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr, Pittsburgh, PA
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 ...
The Landing Hotel at Rivers Casino
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Thu, Oct 2 - Thu, Oct 16
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Oct 2 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Thu, Oct 16, priced at $70 found 2 days ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 18
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Philadelphia Intl. to Pittsburgh Intl., returning Mon, Aug 18, priced at $118 found 1 day ago
Spirit Airlines
Wed, Oct 8 - Sat, Oct 11
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Oct 8 from Logan Intl. to Pittsburgh Intl., returning Sat, Oct 11, priced at $120 found 1 day ago
JetBlue Airways
Fri, Oct 31 - Fri, Nov 7
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 7 hours ago
$121
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Oct 31 from John F. Kennedy Intl. to Pittsburgh Intl., returning Fri, Nov 7, priced at $121 found 7 hours ago