Oakland Vacation Packages

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Your Oakland Vacation

Entertainment, history, art and more … There's so much to experience with a Oakland vacation package. And with the ability to customize your city break, it's guaranteed to be one that's tough to forget. In the mood to explore the sights but not sure where to begin? Any trip to Oakland should include Madill Gaming Center. Don't delay your visit to this destination any longer. Your dream Oakland vacation is just a few clicks away with Expedia.

Top Oakland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Romantic Inn & Suites

Romantic Inn & Suites

2 out of 5
Southwest Dallas
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Dallas (DAL)
6.6/10 (916 reviews)
We had a great time

Reviewed on Nov. 16, 2024

Casa Duro

Casa Duro

5 out of 5
Lower Greenville
per person
Oct 16 - Oct 20
found 2 days ago
Roundtrip flight included
Montreal (YUL) to Dallas (DAL)
9.4/10 Exceptional! (114 reviews)
Fantastic getaway, thank you. Surroundings and ability to work everywhere were awesome, thank you!

Reviewed on Jul. 3, 2025

Hotel Crescent Court

Hotel Crescent Court

5 out of 5
Uptown
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Dallas (DAL)
9.2/10 Wonderful! (1,001 reviews)
Beautiful property! The room was super clean and spacious. The room was stocked with nice bath amenities

Reviewed on Jul. 31, 2025

Virgin Hotels Dallas

Virgin Hotels Dallas

4.5 out of 5
Dallas Design District
per person
Oct 16 - Oct 20
found 2 days ago
Roundtrip flight included
Montreal (YUL) to Dallas (DAL)
9.2/10 Wonderful! (1,124 reviews)
Location was great. They have a curtesy shuttle that will drive you within a 3-mile radius so I able to get a ride to American Airlines center and then walked back that night after a concert. I had an Expedia VIP perk of having $30 off on food but caveat being that when ordering room service, you have to pay an amenity fee which was $25 and the food was >than $30 so not sure the perk is useful when used in this way as I could get something way cheaper elsewhere. My preference is for beds and pillows to be firmer and theirs was quite soft and sunken so did not sleep well. It was quiet and the room was nice overall.

Reviewed on Jul. 27, 2025

Canvas Hotel Dallas

Canvas Hotel Dallas

4 out of 5
South Dallas
per person
Oct 16 - Oct 20
found 2 days ago
Roundtrip flight included
Montreal (YUL) to Dallas (DAL)
8.8/10 Excellent! (2,543 reviews)
Location and the view from the pool was awesome

Reviewed on Aug. 2, 2025

Ready to book your vacation to Oakland?

 

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Oakland Hotel Deals

Willow Springs Marina

Willow Springs Marina

2 out of 5
1401 Willow Springs Rd, Mead, OK
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Aug 3 to Aug 4
CA $105
CA $125 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (202 reviews)
"Our family had a wonderful experience at Willow Springs Marina-Great Cabins, very clean and workers are extremely nice and helpful. Experienced Willow Wipeout and definitely recommend it. Kids absolutely loved the experience and we will be back! We documented our experience on our channel- ..."

Reviewed on Jul. 29, 2025

Willow Springs Marina
Best Western Plus Sand Bass Inn & Suites

Best Western Plus Sand Bass Inn & Suites

2.5 out of 5
827 S 1st St, Madill, OK
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Aug 16 to Aug 17
CA $190
CA $217 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (401 reviews)
Well Taken Care Of and Well Managed
"Despite a little trouble with hotels.com, Dulce and her manager, Bo, reached out to me personally before check in and were able to resolve the trouble and even allowed me to check in early. The hotel was clean enough to make me overlook small cosmetic issues. The room was big and comfortable. The ..."

Reviewed on Jul. 22, 2025

Best Western Plus Sand Bass Inn & Suites
American Inn Madill

American Inn Madill

2 out of 5
601 N 1st Street, Madill, OK
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 3 to Aug 4
CA $124
CA $142 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (340 reviews)
"The staff was very friendly. This was my first stay here and I was pleasantly surprised. The rooms were adequate size and the property was very clean. Nice breakfast. I will stay here again when I go to Madill."

Reviewed on Jul. 16, 2025

American Inn Madill
See all 399 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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Family Vacations
Family Vacations

Discover the most popular places to visit in Oakland

Memorial Park

Explore the great outdoors at Memorial Park, a lovely green space in Madill. You'll find more to see and do in this family-friendly area.

Memorial Park

Frequently asked questions

How much does an Oakland vacation package cost?
Offering excellent value package deals from CA $1,033 on Expedia, you'll be pleasantly surprised at how much a vacation to Oakland costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Oakland?
If you're hoping to snag a cheap Oakland vacation package, consider visiting in January, February and April. You're likely to find lower prices on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to check out all the main sights and explore some hidden spots along the way.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Oakland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically 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 flights and hotels separately. Better still, you can personalize your Oakland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oakland?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Oakland trip.
How to plan a trip to Oakland?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Oakland.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Oakland.
  3. Work out your trip length: Consider how long you want to spend discovering Oakland. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Oakland vacation package that brings all your bookings together.

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