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A white church with a modern design, a large tree in front, and a clear blue sky.

Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Oakland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Oct 22 - Oct 27

    Hu. Hotel + Flight

    Downtown Memphis
    5 nights
    3.5 star property
    8.4/10 - Very good (2,243 reviews)
    Roundtrip • Toronto (YYZ) - Memphis (MEM)
    YYZ - MEM • 1 stop MEM - YYZ • 1 stop
    CA $1,230
    CA $998
    per traveller
    found 21 hours ago
    Hu. Hotel
  • Lobby
    Oct 22 - Oct 27

    The Guest House at Graceland + Flight

    Whitehaven
    5 nights
    4.0 star property
    9.6/10 - Exceptional (2,914 reviews)
    "Wonderful place to stay. Staff was great! Food was delicious!"
    Reviewed August 3, 2026
    Roundtrip • Toronto (YYZ) - Memphis (MEM)
    YYZ - MEM • 1 stop MEM - YYZ • 1 stop
    CA $2,042
    CA $1,537
    per traveller
    found 21 hours ago
    The Guest House at Graceland
  • Bar (on property)
    Oct 22 - Oct 27

    Hotel Pontotoc + Flight

    Downtown Memphis
    5 nights
    2.0 star property
    9.6/10 - Exceptional (33 reviews)
    "Excellent in the boutique hotel space. Vintage and modern combined, lots of beautiful touches throughout. Loved The Dame downstairs!"
    Reviewed July 26, 2026
    Roundtrip • Toronto (YYZ) - Memphis (MEM)
    YYZ - MEM • 1 stop MEM - YYZ • 1 stop
    CA $1,900
    CA $1,507
    per traveller
    found 21 hours ago
    Hotel Pontotoc
  • Luxury Loft, 1 Bedroom, Non Smoking, City View | In-room dining
    Oct 22 - Oct 27

    The Stallion + Flight

    Downtown Memphis
    5 nights
    4.5 star property
    9.8/10 - Exceptional (375 reviews)
    "The room or loft at the Stallion was absolutely amazing! I especially loved the Elvis pictures and the guitar—it was such a nice touch. Everything felt so homey and comfortable. My kids and husband really enjoyed it, and my kids kept raving about how cool this place is. Parking was super easy, both inside and out. It was also super convenient to check in and out. I really appreciated that it had its own washer and dryer and provided the detergent. Everything was spotless."
    Reviewed August 3, 2026
    Roundtrip • Toronto (YYZ) - Memphis (MEM)
    YYZ - MEM • 1 stop MEM - YYZ • 1 stop
    CA $1,477
    CA $1,178
    per traveller
    found 21 hours ago
    The Stallion
  • Exterior
    Oct 22 - Oct 27

    Landing Furnished Apartments Harborside - Memphis + Flight

    North Memphis
    5 nights
    4.0 star property
    10/10 - Exceptional (3 reviews)
    "Great property and location"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YYZ) - Memphis (MEM)
    YYZ - MEM • 1 stop MEM - YYZ • 1 stop
    CA $1,612
    CA $1,350
    per traveller
    found 21 hours ago
    Landing Furnished Apartments Harborside - Memphis

Oakland Hotel Deals

Lobby

Fairfield Inn & Suites by Marriott Memphis Arlington

Fairfield Inn & Suites by Marriott Memphis Arlington
3.0 star property
14.1 km from Oakland
9.6 out of 10, Exceptional, (607 reviews)
The price is CA $144
CA $172 total
includes taxes & fees
Aug 16 - Aug 17
Fairfield Inn & Suites by Marriott Memphis Arlington
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.
See all properties in Oakland

Frequently Asked Questions

How much does an Oakland vacation package cost?

You can snap up a vacation package to this popular destination from CA $998 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.