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

Ready to book your vacation to Oakland?

 

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Oakland Hotel Deals

The Westin Southfield Detroit

The Westin Southfield Detroit

4 out of 5
1500 Town Center Southfield MI
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 12 to Jul 13
CA $197
CA $225 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (1,369 reviews)
"Tango restaurant and staff was awesome."

Reviewed on Jul 7, 2026

The Westin Southfield Detroit
Radisson Hotel Southfield-Detroit

Radisson Hotel Southfield-Detroit

3 out of 5
26555 Telegraph Rd Southfield MI
Fully refundable
The price is CA $156 per night from Jul 22 to Jul 23
CA $156
CA $177 total
Jul 22 - Jul 23
includes taxes & fees
7.4/10 Good! (1,009 reviews)
"Management was unavailable during the checkout process. My Mother’s jewelry had been stolen out of her room, and we wanted to check out early. We waited for three hours for a manager to approve our early checkout, but we were never assisted in recovering the jewelry. We had to call the police ourselves ..."

Reviewed on Jul 7, 2026

Radisson Hotel Southfield-Detroit
Holiday Inn Express and Suites Detroit/Sterling Heights by IHG

Holiday Inn Express and Suites Detroit/Sterling Heights by IHG

2.5 out of 5
8515 15 Mile Road Sterling Heights MI
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 3 to Aug 4
CA $160
CA $177 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,023 reviews)
"The staff are really good and the breakfast good as well"

Reviewed on Jul 8, 2026

Holiday Inn Express and Suites Detroit/Sterling Heights by IHG
See all 971 properties in Oakland
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.
All Inclusive Vacations
All Inclusive Vacations
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Stay near popular Oakland attractions

Addison Oaks County Park

8.0/10 (2 reviews)
Explore the great outdoors at Addison Oaks County Park, a lovely green space in Oakland. Experience the area's great live music and acclaimed theater scene.
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Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Oakland costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oakland?
If you're looking to snag a cheap Oakland vacation package, consider planning a trip in January, February and November. You'll generally find better prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Oakland?
Typically, a handful of days is enough to explore the major sights during your Oakland vacation. But if you want to have time to rest or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Oakland?
It's easy to see why an Oakland vacation is on the to-do list of many travellers. Leading attractions like Addison Oaks County Park are just the start of what you can explore here.
How to find the best Oakland package deals?
Bagging a cheap Oakland package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-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 generally lower.
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 individually. Better still, you can personalize your Oakland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Oakland?
If you're considering a spontaneous Oakland vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Oakland?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Oakland.
  2. Plan your budget wisely: As well as the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Oakland.
  3. Determine how many days away: Start by listing all the sights and activities you want to experience in Oakland. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick an Oakland vacation package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.