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 New York Times Square
Manhattan
CA $1,672
per person
Oct 9 - Oct 13
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
Facility can use more maintaining. Shower floor was cracked, door was leaking, no one came to clean the room in 4 days, staff did not try to accommodate our needs.
Reviewed on Aug 7, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,509
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
This was an excellent hotel in a perfect location in NYC! The staff was incredible! The only problem was waiting for the elevators during breakfast time. They close an entire elevator just for the breakfast crowd, and we had to wait for nearly 30 minutes to get our luggage down to check out because every elevator that stopped on our floor was already full. Minor inconvenience, just make sure to plan your time around that. Everything else was fabulous! (Except for the weird videos in the front lobby... who wants to watch someone rub sunscreen on another person's back??? So bizarre!)
Reviewed on Aug 7, 2026
Hotel St. James
Manhattan
CA $1,123
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,689 reviews)
We enjoyed the clean and very quiet room, with an updated bathroom. Staff was friendly and helpful and the location was perfect.
Reviewed on Aug 7, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands
350 Lighting Way Secaucus NJ
Fully refundableReserve now, pay when you stay
CA $213
CA $251 total
Aug 9 - Aug 10
includes taxes & fees
La Quinta Inn & Suites by Wyndham Clifton/Rutherford
265 Route 3 East Clifton NJ
Fully refundableReserve now, pay when you stay
CA $155
CA $178 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (3,543 reviews)
"The front desk staff was so helpful and insightful on things to do with my children on the spectrum this is a great place to stay with family I definitely will be coming back"
Reviewed on Aug 7, 2026
Harmony Suites
455 Plaza Dr Secaucus NJ
Fully refundableReserve now, pay when you stay
CA $167
CA $197 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (3,631 reviews)
"Clean room breakfast was good."
Reviewed on Aug 7, 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 $689 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.
