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Oakland Vacation Packages

Oakland Flight + Hotel packages

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
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this 4-star 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 PPG Paints Arena and Rivers Casino are located nearby.
Hawthorn Suites by Wyndham Wheeling at the Highlands

Hawthorn Suites by Wyndham Wheeling at the Highlands

3.5 out of 5
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Triadelphia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Highlands and Highlands Sports Complex are located nearby.
Homewood Suites by Hilton Pittsburgh Southpointe

Homewood Suites by Hilton Pittsburgh Southpointe

3 out of 5
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this 3-star business-friendly hotel in Canonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southpointe Town Center and Printscape Arena at Southpointe are located nearby.
Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this 3.5-star 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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this aparthotel in Pittsburgh. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 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.
Fairfield Inn & Suites by Marriott Pittsburgh Neville Island

Fairfield Inn & Suites by Marriott Pittsburgh Neville Island

2.5 out of 5
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Sheraton Pittsburgh Hotel at Station Square

Sheraton Pittsburgh Hotel at Station Square

3.5 out of 5
South Shore
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
Oakland
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Residence Inn by Marriott Pittsburgh North Shore

Residence Inn by Marriott Pittsburgh North Shore

3 out of 5
North Shore
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)

5-7 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Hawthorn Suites by Wyndham Wheeling at the Highlands

Hawthorn Suites by Wyndham Wheeling at the Highlands

3.5 out of 5
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

4.5 out of 5
Downtown Pittsburgh
per person
Feb 26 - Mar 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Feb 26 - Mar 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)

Cheap Hotel Deals in Oakland

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
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
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
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Hotel Indigo Pittsburgh University-Oakland, an IHG Hotel

Hotel Indigo Pittsburgh University-Oakland, an IHG Hotel

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, an IHG Hotel
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
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
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 ...
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Homewood Suites by Hilton Pittsburgh Downtown

Homewood Suites by Hilton Pittsburgh Downtown

3 out of 5
1410 Smallman Street, 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 ...
Homewood Suites by Hilton Pittsburgh Downtown
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
Tue, Feb 4 - Tue, Feb 4
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Feb 4 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Tue, Feb 4, priced at $58 found 19 hours ago
Spirit Airlines
Wed, Mar 5 - Wed, Mar 12
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$86 Roundtrip, found 2 days ago
$86
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Mar 5 from Logan Intl. to Pittsburgh Intl., returning Wed, Mar 12, priced at $86 found 2 days ago
Frontier Airlines
Tue, Apr 1 - Wed, Apr 9
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 1 from John F. Kennedy Intl. to Pittsburgh Intl., returning Wed, Apr 9, priced at $120 found 1 day ago
Spirit Airlines
Wed, Feb 12 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Feb 12 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Tue, Feb 25, priced at $124 found 2 days ago