Oakland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
Our vacation packages to Oakland give you countless opportunities to delve into new sights, sounds and sensations. And with all the travel planning worked out, you can breathe easy and enjoy your city getaway without a worry in the world. Every trip to Oakland needs a well-designed itinerary. Fill yours with leading attractions like Campgaw Mountain Ski Area, High Mountain Park and Lake Erskine. Stop daydreaming and start adventuring. Explore the range of options on Expedia today and put your Oakland vacation plans into action!
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,011
per person
Nov 27 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.
Reviewed on Oct 25, 2026
Night Hotel Broadway
Manhattan
CA $1,345
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,714 reviews)
El lobby y áreas comunes del hotel estaban sucias y descuidadas. El aire acondicionado del cuarto muy ruidoso. Guardaron nuestras maletas antes del check in en un cuarto lleno de escombros y polvo.
Reviewed on Oct 25, 2026
The Kitano Hotel New York
Manhattan
CA $1,661
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (2,390 reviews)
All elements were excellent. The style of the hotel is simple and pleasing. The staff were exceptionally pleasant and helpful. The hotel had no faults, in my experience.
Reviewed on Oct 26, 2026
Eurostars Wall Street
Manhattan
CA $1,570
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
It is definitely older, Only 1 elevator was working, The fan was not working in the bathroom. The floors in the rooms need replacing as the vinyl flooring was peeling up. The bedding and heating was fine. But definitely not worth the 732.00 per night I paid.
Reviewed on Oct 24, 2026
Hotel Riu Plaza New York Times Square
Manhattan
CA $1,383
per person
Dec 9 - Dec 11
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Location is superb. Gym is well equipped and in good repair. Breakfast was good - but ridiculously busy. Queues every day. We had two queen beds and a sofa bed which was fine for a family of four. The housekeeping was rubbish - they only cleaned the room one day in four nights, and no change of towels. When they did clean it they put the sofa bed away and removed the bedding. We got back late after a concert and waited an hour and a half for extra bedding to be brought up - despite multiple calls to the front desk-
Was really disappointing given it was late and the kids were tired. Put a
Dampener on what would have been a good hotel experience.
Reviewed on Oct 26, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
La Quinta Inn & Suites by Wyndham Clifton/Rutherford
265 Route 3 East Clifton NJ
Fully refundableReserve now, pay when you stay
CA $185
CA $212 total
Nov 23 - Nov 24
includes taxes & fees
Garner Hotel North Bergen - NYC Gateway by IHG
2750 Tonnelle Ave North Bergen NJ
Fully refundable
CA $154
CA $181 total
Nov 16 - Nov 17
includes taxes & fees
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands
350 Lighting Way Secaucus NJ
Fully refundableReserve now, pay when you stay
CA $157
CA $184 total
Nov 3 - Nov 4
includes taxes & fees
6.8/10 (2,480 reviews)
"En la habitación había problemas con el agua caliente y huelia a humedad"
Reviewed on Oct 26, 2026
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.
Stay near popular Oakland attractions
Crystal Lake Beach Club
Why not spend a lazy afternoon at Crystal Lake Beach Club during your trip to Oakland? Amble around the area's forest or visit its shops.
Frequently asked questions
How much does an Oakland vacation package cost?
You'll find cheap prices from CA $1,011 on Expedia for your Oakland break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
If you're hoping to snag a cheap Oakland vacation package, consider planning a trip in January, February and March. You'll typically find lower rates on accommodations and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Oakland?
The ideal length for your Oakland vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to go to all the main attractions and discover some hidden gems along the way.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can customize your Oakland escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates finalized, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Oakland?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Oakland.
- Plan your budget wisely: In addition to the price of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may come up during your trip to Oakland.
- Work out your trip length: Consider how long you'd like to spend discovering Oakland. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Oakland vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
