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
Skip the hassle of organizing your next grand adventure with a Oakland vacation package. Whether you're interested in its art, food, architecture or something else, this city offers limitless opportunities for discovery. Ready to see the sights? Spend some time enjoying major attractions such as Confederate Cemetery during your trip to Oakland. Whatever your travel plans or budget, organizing a tailored Oakland vacation is a breeze with Expedia.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Stallion
Downtown Memphis
CA $1,155
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Memphis (MEM)
9.8/10 Exceptional! (423 reviews)
Perfect studio apartment with modern amenities. I appreciate seeing old buildings being refurbished back to new life. Within a block to the Blues Hall of Fame Museum and the National Civil Rights Museum; both a "must visit" attractions in Memphis.
Reviewed on Oct 2, 2026
Hotel Pontotoc
Downtown Memphis
CA $1,329
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Memphis (MEM)
9.8/10 Exceptional! (42 reviews)
Room was charming, clean and well taken care of. The staff was wonderful. Breakfast was a delight. You filled out your order the night before and hung it on your door. The next morning at the time of your choosing it is delivered. I opened the door and there was a man with a tray filled with our order. The pastries were warm and the smell was amazing. I can't say enough wonderful things. We would definitely stay here again.
Reviewed on Sep 21, 2026
Landing Furnished Apartments Harborside - Memphis
North Memphis
CA $1,405
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Memphis (MEM)
9.8/10 Exceptional! (6 reviews)
Great for entire family. Lots of room with space for quiet time. Not enough toiletries, ran out first day which was disappointing
Reviewed on Sep 7, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Lakefront Tiny Cabin Near Memphis + Hot Tub
Oakland TN
CA $121
CA $290 total
Oct 22 - Oct 23
includes taxes & fees
10/10 Exceptional! (48 reviews)
"Really great"
Reviewed on Sep 27, 2026
Best Western Plus Galleria Inn & Suites
8635 Us Highway 64 Memphis TN
Fully refundableReserve now, pay when you stay
CA $105
CA $128 total
Oct 5 - Oct 6
includes taxes & fees
8/10 Very good! (1,214 reviews)
"We had to change rooms upon arrival because a/c was out for one. The ice machine did not work. There are ramps on all hallways Dirty bathrooms 👎"
Reviewed on Oct 2, 2026
Hyatt Place Memphis/Wolfchase Galleria
7905 Giacosa Pl Memphis TN
Fully refundableReserve now, pay when you stay
CA $134
CA $162 total
Oct 11 - Oct 12
includes taxes & fees
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.
Frequently asked questions
How much does an Oakland vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,155 on Expedia. However, how much your vacation to Oakland costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Oakland?
The off-season is the best time to head to Oakland if you're hoping to keep costs down. Another tip for getting cheap Oakland vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Oakland?
The ideal duration of your Oakland vacation depends on what you'd like to see. Generally, a few days to a week will give you time to go to all the leading attractions and explore some hidden gems along the way.
How to find the best Oakland package deals?
Use Expedia's handy filters to help you find some fabulous Oakland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Oakland package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights separately. Better still, you can customize your Oakland escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals 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 early as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Oakland?
- Choose when to travel: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Oakland.
- Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Oakland.
- Decide how long to go away for: Now that you're up to speed on Oakland, you can figure out the ideal length of your vacation. Pull together a rough plan and allocate enough time to get through everything on your must-do list.
- Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the ideal Oakland vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
