Oakwood Vacations from $529

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The Latest Oakwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Encore Inn Inglewood

Encore Inn Inglewood

2.5 out of 5
Lockhaven
Price was $1,698, price is now $529 per person
$529
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Los Angeles (LAX)
6.4/10 (159 reviews)
Clean room w/ a shower.

Reviewed on Jan 2, 2026

Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was $2,206, price is now $779 per person
$779
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,537, price is now $564 per person
$564
per person
Jul 9 - Jul 12
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
6/10 (2 reviews)
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was $1,479, price is now $552 per person
$552
per person
Jul 17 - Jul 20
found 5 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Miami (MIA)
9/10 Wonderful! (2 reviews)
Great place and location! The pool was amazing.

Reviewed on May 9, 2026

MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $1,488, price is now $612 per person
$612
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
2/10 (2 reviews)
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Oakwood Hotel Deals

Lucky Star Casino Hotel & Convention Center

Lucky Star Casino Hotel & Convention Center

3.5 out of 5
1407 S Clarence Nash Blvd Watonga OK
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $111 total per night from May 24 to May 25
$111 total
May 24 - May 25
Total with taxes and fees
Lucky Star Casino Hotel & Convention Center
Small Mansion near State Park and Casino

Small Mansion near State Park and Casino

Watonga OK
$624 nightly
The price is $714 total per night from May 18 to May 19
$714 total
May 18 - May 19
Total with taxes and fees
9.6/10 Exceptional! (13 reviews)
Pet friendly! Very accommodating and helpful.

Reviewed on Apr 29, 2026

Small Mansion near State Park and Casino
The Redbud Cabin at Roman Nose

The Redbud Cabin at Roman Nose

Watonga OK
$150 nightly
The price is $163 total per night from May 18 to May 19
$163 total
May 18 - May 19
Total with taxes and fees
10/10 Exceptional! (35 reviews)
Enjoyed our stay here. Owner was very quick to respond to any questions. Couldn’t ask for more.

Reviewed on Apr 22, 2026

The Redbud Cabin at Roman Nose
See all 13 properties in Oakwood
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.

Find the Best Oakwood Vacation Packages

Oakwood Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does an Oakwood vacation package cost?
You'll find cheap prices from $529 on Expedia for your Oakwood escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oakwood costs.
What are the cheapest months to go to Oakwood?
You can generally find lower prices and greater availability in December, January and February. Browse our cheap Oakwood vacation packages and you could land some excellent off-season deals.
How many days is enough for Oakwood?
With a well-organized itinerary, you can easily tick off the top Oakwood sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Oakwood vacation for longer.
How to find the best Oakwood package deals?
Use Expedia's handy filters to find some of the best Oakwood package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Oakwood package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oakwood vacation as a package?
You can enjoy significant savings on your next Oakwood break by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Oakwood?
If you're planning an impromptu Oakwood getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oakwood vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Oakwood trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.