Search Deals on
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
Price was $678, price is now $526 per person
$526
per person
May 29 - Jun 4
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,369, price is now $1,007 per person
$1,007
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,102, price is now $815 per person
$815
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
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 the convenient parking in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.
Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Save 100% on your flight
Price was $1,375, price is now $1,058 per person
$1,058
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
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 staff in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,372, price is now $1,064 per person
$1,064
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
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 rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Home2 Suites by Hilton Pittsburgh / McCandless, PA

Home2 Suites by Hilton Pittsburgh / McCandless, PA

3 out of 5
North Side
Save 100% on your flight
Price was $922, price is now $726 per person
$726
per person
Jun 11 - Jun 16
found 16 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ross Park Mall and North Park are located nearby.
Home2 Suites by Hilton Pittsburgh Area Beaver Valley

Home2 Suites by Hilton Pittsburgh Area Beaver Valley

3 out of 5
Save 100% on your flight
Price was $852, price is now $672 per person
$672
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Monaca. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Cinemark Center Township Marketplace and Beaver Area Heritage Museum are located nearby.
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Save 100% on your flight
Price was $1,628, price is now $1,285 per person
$1,285
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Stay at this vacation home in Pittsburgh. Enjoy free WiFi, a free airport shuttle, and a garden. Popular attractions Acrisure Stadium and PNC Park are located nearby.

3-4 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $489, price is now $365 per person
$365
per person
Jun 8 - Jun 11
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $881, price is now $660 per person
$660
per person
May 28 - May 31
found 14 hours ago
Roundtrip 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
Price was $907, price is now $695 per person
$695
per person
Jun 8 - Jun 11
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was $613, price is now $479 per person
$479
per person
Jun 8 - Jun 11
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)

5-7 Night Vacations in Oakland

Price found within the past 48 hours. Click for updated prices.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,102, price is now $815 per person
$815
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,369, price is now $1,007 per person
$1,007
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Save 100% on your flight
Price was $1,375, price is now $1,058 per person
$1,058
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,372, price is now $1,064 per person
$1,064
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) 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
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
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
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
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
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 ...
Opens in a new windowPittsburgh Marriott City Center
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 ...
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.

Spirit Airlines
Wed, May 13 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$142 Roundtrip, found 12 hours ago
$142
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Mon, May 18, priced at $142 found 12 hours ago
American Airlines
Tue, May 26 - Wed, May 27
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$161 Roundtrip, found 11 hours ago
$161
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, May 26 from John F. Kennedy Intl. to Pittsburgh Intl., returning Wed, May 27, priced at $161 found 11 hours ago
United
Fri, May 29 - Mon, Jun 1
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select United flight, departing Fri, May 29 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Mon, Jun 1, priced at $161 found 4 days ago
American Airlines
Tue, Jun 2 - Tue, Jun 16
LGA
LaGuardia
PIT
Pittsburgh Intl.
$171 Roundtrip, found 8 hours ago
$171
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Jun 2 from LaGuardia to Pittsburgh Intl., returning Tue, Jun 16, priced at $171 found 8 hours ago