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Oakland Vacation Packages

Oakland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Suburban Studios Triadelphia - Wheeling at The Highlands

Suburban Studios Triadelphia - Wheeling at The Highlands

2 out of 5
Price was $304, price is now $234 per person
$234
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Triadelphia. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Oglebay Park and The Highlands are located nearby.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $533, price is now $372 per person
$372
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Microtel Inn & Suites by Wyndham Wheeling at Highlands

Microtel Inn & Suites by Wyndham Wheeling at Highlands

2 out of 5
Price was $364, price is now $278 per person
$278
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Triadelphia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oglebay Park and The Highlands are located nearby.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $470, price is now $366 per person
$366
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
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 staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Mountaineer Casino Resort

Mountaineer Casino Resort

3.5 out of 5
Price was $508, price is now $397 per person
$397
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this spa resort in New Cumberland. Enjoy free WiFi, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mountaineer Casino and Mountaineer Racetrack are located nearby.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $441, price is now $347 per person
$347
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Acrisure Stadium and PNC Park are located nearby.
SpringHill Suites by Marriott Pittsburgh Washington

SpringHill Suites by Marriott Pittsburgh Washington

3 out of 5
Price was $363, price is now $293 per person
$293
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this 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.
Cambria Hotel Pittsburgh - Downtown

Cambria Hotel Pittsburgh - Downtown

3 out of 5
Downtown Pittsburgh
Price was $487, price is now $401 per person
$401
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
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 staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

3-4 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Suburban Studios Triadelphia - Wheeling at The Highlands

Suburban Studios Triadelphia - Wheeling at The Highlands

2 out of 5
Price was $304, price is now $234 per person
$234
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $533, price is now $372 per person
$372
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Microtel Inn & Suites by Wyndham Wheeling at Highlands

Microtel Inn & Suites by Wyndham Wheeling at Highlands

2 out of 5
Price was $364, price is now $278 per person
$278
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $470, price is now $366 per person
$366
per person
Jan 17 - Jan 21
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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Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
3341 Forbes Ave 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 breakfast and the helpful ...
Opens in a new windowResidence Inn Pittsburgh Oakland/University Place
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 ...
Opens in a new windowHampton Inn Pittsburgh University/Medical Center
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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Opens in a new windowWyndham Grand 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
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
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
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.

Delta
Wed, Jan 28 - Thu, Feb 12
LGA
LaGuardia
PIT
Pittsburgh Intl.
$121 Roundtrip, found 15 hours ago
$121
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Jan 28 from LaGuardia to Pittsburgh Intl., returning Thu, Feb 12, priced at $121 found 15 hours ago
American Airlines
Sat, Jan 31 - Sat, Feb 7
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 22 hours ago
$121
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Jan 31 from John F. Kennedy Intl. to Pittsburgh Intl., returning Sat, Feb 7, priced at $121 found 22 hours ago
United
Tue, Jan 20 - Tue, Jan 27
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$121 Roundtrip, found 15 hours ago
$121
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Jan 20 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Tue, Jan 27, priced at $121 found 15 hours ago
Spirit Airlines
Sat, Feb 7 - Mon, Feb 9
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$123 Roundtrip, found 4 hours ago
$123
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Feb 7 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Mon, Feb 9, priced at $123 found 4 hours ago