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Oakland Vacation Packages

Oakland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
SpringHill Suites by Marriott Pittsburgh Washington

SpringHill Suites by Marriott Pittsburgh Washington

3 out of 5
Price was $463, price is now $381 per person
$381
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
Stay at this 3-star 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.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $986, price is now $608 per person
$608
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,247, price is now $870 per person
$870
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
Stay at this 4-star hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $1,301, price is now $920 per person
$920
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
Stay at this 4.5-star luxury hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
DoubleTree by Hilton Pittsburgh Airport

DoubleTree by Hilton Pittsburgh Airport

4 out of 5
Price was $894, price is now $672 per person
$672
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
Stay at this 4-star business-friendly hotel in Coraopolis. Enjoy free WiFi, free parking, and breakfast (surcharge). 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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $1,008, price is now $768 per person
$768
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) 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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $756, price is now $579 per person
$579
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) 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.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was $1,281, price is now $989 per person
$989
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.

3-4 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $453, price is now $351 per person
$351
per person
Dec 12 - Dec 15
found 2 hours ago
Roundtrip flight included
Dallas (DFW) 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
Price was $805, price is now $558 per person
$558
per person
Dec 12 - Dec 15
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $531, price is now $369 per person
$369
per person
Dec 12 - Dec 15
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $723, price is now $539 per person
$539
per person
Dec 12 - Dec 15
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)

5-7 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $876, price is now $554 per person
$554
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,247, price is now $870 per person
$870
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $1,301, price is now $920 per person
$920
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
DoubleTree by Hilton Pittsburgh Airport

DoubleTree by Hilton Pittsburgh Airport

4 out of 5
Price was $894, price is now $672 per person
$672
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Houston (IAH) 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 ...
Opens in a new windowCourtyard by Marriott Pittsburgh University 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 ...
Opens in a new windowHotel Indigo Pittsburgh University-Oakland by IHG
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. ...
Opens in a new windowThe Oaklander Hotel, Autograph Collection
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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 ...
Opens in a new windowResidence 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 ...
Opens in a new windowWyndham 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 ...
Opens in a new windowOmni William Penn Hotel
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
One Bigelow Square, Pittsburgh, PA
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 ...
Opens in a new windowDoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
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
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 ...
Opens in a new windowJoinery Hotel Pittsburgh, Curio Collection by Hilton
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.

American Airlines
Tue, Dec 2 - Tue, Dec 9
LGA
LaGuardia
PIT
Pittsburgh Intl.
$107 Roundtrip, just found
$107
Roundtrip
just found
Select American Airlines flight, departing Tue, Dec 2 from LaGuardia to Pittsburgh Intl., returning Tue, Dec 9, priced at $107 just found
United
Tue, Jan 20 - Tue, Jan 27
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jan 20 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Tue, Jan 27, priced at $110 found 3 days ago
Frontier Airlines
Mon, Dec 1 - Thu, Dec 4
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 1 from Philadelphia Intl. to Pittsburgh Intl., returning Thu, Dec 4, priced at $112 found 1 day ago
American Airlines
Tue, Feb 3 - Sat, Feb 7
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 3 from John F. Kennedy Intl. to Pittsburgh Intl., returning Sat, Feb 7, priced at $121 found 1 day ago