Oakland Vacation Packages for 2026

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Top Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
0.5 km from Oakland
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 ...
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
1.37 km from Oakland
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 ...
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard Pittsburgh PA
0.38 km from Oakland
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. ...
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
4.02 km from Oakland
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 ...
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
8.91 km from Oakland
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 ...
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
5.27 km from Oakland
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 ...
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd Coraopolis PA
23.41 km from Oakland
Book a stay at this family-friendly hotel in Coraopolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
2.8 km from Oakland
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 ...
Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

4 out of 5
745 Grant Street Pittsburgh PA
3.01 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
710 Aviation Avenue Pittsburgh PA
26.08 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place Pittsburgh PA
3.16 km from Oakland
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 ...
Hyatt Place Pittsburgh-North Shore

Hyatt Place Pittsburgh-North Shore

3 out of 5
260 North Shore Drive Pittsburgh PA
4.16 km from Oakland
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 ...
Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
250 Forbes Avenue Pittsburgh PA
3.58 km from Oakland
Stay at this hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
177 40th Street Pittsburgh PA
2.9 km from Oakland
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
120 S Whitfield St Pittsburgh PA
3.42 km from Oakland
Stay at this hotel in Pittsburgh. Enjoy free WiFi, a 24-hour business center, and cable TV channels. Our guests praise the helpful staff and the clean rooms ...
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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

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Dec 9 - Wed, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 9 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Wed, Dec 16, priced at $189 found 5 days ago
Frontier Airlines
Tue, Jan 12 - Sat, Jan 23
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$195 Roundtrip, found 16 hours ago
$195
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Jan 12 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Sat, Jan 23, priced at $195 found 16 hours ago
American Airlines
Wed, Dec 9 - Wed, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Dec 9 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Wed, Dec 16, priced at $199 found 5 days ago
United
Wed, Dec 9 - Wed, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select United flight, departing Wed, Dec 9 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Wed, Dec 16, priced at $199 found 5 days ago
Delta
Tue, Jan 12 - Sat, Jan 23
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$199 Roundtrip, found 16 hours ago
$199
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Jan 12 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Sat, Jan 23, priced at $199 found 16 hours ago