Search Deals onOakland Vacation Packages
Oakland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Oaktown Roost
Price was $354, price is now $262 per person
$262
per person
Dec 12 - Dec 15
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Oakland (OAK)
Stay at this hotel in Oakland. Enjoy free WiFi, parking (surcharge), and a garden. Popular attractions Fox Theater and Jack London Square are located nearby.
Claremont Resort & Club
Price was $2,020, price is now $1,406 per person
$1,406
per person
Jan 23 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Oakland (OAK)
Book a stay at this luxury hotel in Berkeley. Enjoy 3 outdoor pools, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Fox Theater and Jack London Square are located nearby.
Fantastic location with great view, on-site restaurant, parking and club access. Lobby was decorated for Christmas.
Reviewed on Nov 10, 2026
Vino Bello Resort
Price was $1,048, price is now $733 per person
$733
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Oakland (OAK)
Book a stay at this spa hotel in Napa. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Napa Valley Wine Train and Trinitas Cellars are located nearby.
SENZA Hotel
Save 100% on your flight
Price was $1,570, price is now $1,119 per person
$1,119
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Oakland (OAK)
Stay at this hotel in Napa. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Napa Valley Wine Train and Trefethen Family Vineyard are located nearby.
Breakfast was delicious, the massage excellent and relaxing, the hot tub was great for a soak. We enjoyed walking to Don Giovannis for lunch and it's proximity to wineries (they're spread apart, you'll need an Uber). The garden sculptures are fun and whimsical, and the fountains relaxing.
Reviewed on Nov 10, 2026
DoubleTree by Hilton Hotel Berkeley Marina
Price was $922, price is now $666 per person
$666
per person
Jan 23 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Oakland (OAK)
Book a stay at this business-friendly hotel in Berkeley. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Fox Theater and Jack London Square are located nearby.
Big & Beautiful 6 Bedroom 2.5 Bath
Price was $1,791, price is now $1,303 per person
$1,303
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Oakland (OAK)
Stay at this apartment in Oakland. Enjoy free WiFi, Netflix, and in-room washers/dryers. Popular attractions Fox Theater and Jack London Square are located nearby.
This property had a double-booking issue. When we arrived on September 7, other guests were already staying in the house, and they showed us their valid Expedia booking until September 13.
We attempted to contact the host via calls and messages, but received no response at all. We reached out to Expedia customer service immediately, yet the situation was not resolved. We were forced to book a new hotel last minute, which brought unexpected extra costs.
In the end, Expedia did not provide any compensation. I am very disappointed with the handling of this incident. Anyone considering booking this place should prepare for the worst-case scenario.
Reviewed on Sep 10, 2026
Carneros Resort and Spa
Save 100% on your flight
Price was $2,251, price is now $1,658 per person
$1,658
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Oakland (OAK)
Book a stay at this luxury hotel in Napa. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Napa Valley Wine Train and Domaine Carneros are located nearby.
Everything is excellent
Reviewed on Nov 7, 2026
Alila Napa Valley, a Hyatt Luxury Resort
Save 100% on your flight
Price was $2,640, price is now $1,951 per person
$1,951
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Oakland (OAK)
Book a stay at this luxury resort in St. Helena. Enjoy free WiFi, a full-service spa, and an attached winery. Popular attractions Castello di Amorosa and Beringer Vineyards are located nearby.
Amaizing
Reviewed on Oct 17, 2026
Oakland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Oakland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Dec 9 - Wed, Dec 9
LAX
Los Angeles Intl.
SFO
San Francisco Intl.
$38 Roundtrip, found 2 hours ago
$38
Roundtrip
found 2 hours ago
Thu, Dec 3 - Mon, Dec 7
LAX
Los Angeles Intl.
SJC
Norman Y. Mineta San Jose Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Wed, Dec 2 - Mon, Dec 21
LAX
Los Angeles Intl.
OAK
Oakland Intl.
$135 Roundtrip, found 12 hours ago
$135
Roundtrip
found 12 hours ago
Wed, Dec 9 - Tue, Jan 12
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$250 Roundtrip, found 1 hour ago
$250
Roundtrip
found 1 hour ago
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