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Oakland Vacation Packages

Oakland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Extended Stay America Premier Suites Pittsburgh Cranberry To

Extended Stay America Premier Suites Pittsburgh Cranberry To

2.5 out of 5
Price was $412, price is now $332 per person
$332
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Cranberry Township. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions UPMC Lemieux Sports Complex and Seven Fields Nature Preserve are located nearby.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $952, price is now $582 per person
$582
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
Stay at this 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.
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

2 out of 5
Price was $521, price is now $410 per person
$410
per person
May 8 - May 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly motel in Coraopolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the property condition in our reviews. Popular attractions The Mall at Robinson and UPMC Events Center are located nearby.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $949, price is now $754 per person
$754
per person
May 8 - May 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this 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.
DoubleTree by Hilton Pittsburgh Airport

DoubleTree by Hilton Pittsburgh Airport

4 out of 5
Price was $696, price is now $575 per person
$575
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
Book a stay at this 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.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $610, price is now $506 per person
$506
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
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 our reviews. Popular attractions PNC Park and PPG Paints Arena are located nearby.
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $868, price is now $731 per person
$731
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
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 the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Hampton Inn Pittsburgh/Greentree

Hampton Inn Pittsburgh/Greentree

2.5 out of 5
Price was $1,022, price is now $880 per person
$880
per person
May 9 - May 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and PPG Paints Arena are located nearby.

3-4 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Pittsburgh Airport

Wyndham Garden Pittsburgh Airport

3 out of 5
Price was $444, price is now $387 per person
$387
per person
May 8 - May 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

2 out of 5
Price was $521, price is now $410 per person
$410
per person
May 8 - May 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
DoubleTree by Hilton Pittsburgh Airport

DoubleTree by Hilton Pittsburgh Airport

4 out of 5
Price was $696, price is now $575 per person
$575
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
TownePlace Suites by Marriott Pittsburgh Cranberry Township

TownePlace Suites by Marriott Pittsburgh Cranberry Township

3 out of 5
Price was $573, price is now $515 per person
$515
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
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
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 ...
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
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. ...
Opens in a new windowThe Oaklander Hotel, Autograph Collection
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Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl 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 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 luxury hotel in Pittsburgh. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowOmni William Penn Hotel
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
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 ...
Opens in a new windowJoinery Hotel Pittsburgh, Curio Collection by Hilton
Etage Executive Living

Etage Executive Living

3.5 out of 5
424 Stanwix St. Pittsburgh PA
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Our guests praise the helpful staff and ...
Opens in a new windowEtage Executive Living
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 PNC Park and PPG Paints Arena ...
Opens in a new windowThe 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.

JetBlue Airways
Tue, May 5 - Tue, May 19
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$151 Roundtrip, found 3 hours ago
$151
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, May 5 from John F. Kennedy Intl. to Pittsburgh Intl., returning Tue, May 19, priced at $151 found 3 hours ago
United
Tue, Jun 9 - Wed, Jun 10
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Jun 9 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Wed, Jun 10, priced at $151 found 2 hours ago
Delta
Tue, Apr 21 - Wed, Apr 22
LGA
LaGuardia
PIT
Pittsburgh Intl.
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Apr 21 from LaGuardia to Pittsburgh Intl., returning Wed, Apr 22, priced at $160 found 5 hours ago
Spirit Airlines
Thu, Apr 23 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Apr 23 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Sat, Apr 25, priced at $160 found 2 hours ago