Red Oak Vacations from $368

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The Latest Red Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $521, price is now $368 per person
$368
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
8.8/10 Excellent! (828 reviews)
Location, location, location with an amazing view of the pond. Loved interacting with the horses.

Reviewed on Jul 13, 2026

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $919, price is now $453 per person
$453
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
8.6/10 Excellent! (1,001 reviews)
I had an absolute blast here. The rooms are beautiful and impeccably clean. Staff is excellent and very helpful. We came for a staycation and will be back!

Reviewed on Jul 12, 2026

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $759, price is now $485 per person
$485
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
This was an amazing place and was priced very reasonably.

Reviewed on Jul 13, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $893, price is now $644 per person
$644
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
My friend and I had an amazing time!!

Reviewed on Jul 13, 2026

Wedmore Place

Wedmore Place

3.5 out of 5
Price was $821, price is now $595 per person
$595
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Richmond (RIC)
9.4/10 Exceptional! (1,000 reviews)
Cool place.

Reviewed on Jul 13, 2026

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Red Oak Hotel Deals

Best Western Plus South Hill Inn

Best Western Plus South Hill Inn

3 out of 5
101 Thompson St La Crosse VA
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $105 total per night from Jul 30 to Jul 31
$105 total
Jul 30 - Jul 31
Total with taxes and fees
8.8/10 Excellent! (257 reviews)
"Check in easy. Room was clean and ready upon arrival. Breakfast was hot and ready. Will return soon."

Reviewed on Jul 7, 2026

Best Western Plus South Hill Inn
Crewe Boutique Inn

Crewe Boutique Inn

2.5 out of 5
16092 W Colonial Trail Hwy Crewe VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $97 total per night from Aug 11 to Aug 12
$97 total
Aug 11 - Aug 12
Total with taxes and fees
8.8/10 Excellent! (222 reviews)
"Everything was actually great enjoyed myself had a well time. Pool was clean room was clean. Breakfast was decent."

Reviewed on Jul 13, 2026

Crewe Boutique Inn
Inn at Blackstone

Inn at Blackstone

2.5 out of 5
707 4th Street Blackstone VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $127 total per night from Jul 21 to Jul 22
$127 total
Jul 21 - Jul 22
Total with taxes and fees
9.2/10 Wonderful! (389 reviews)
"The ac didn’t work at all and there was a nail sticking out in our floor I was given a hammer to address the situation"

Reviewed on Jul 8, 2026

Inn at Blackstone
See all 468 properties in Red Oak
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 Red Oak Vacation Packages

Red Oak Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)

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Frequently asked questions

How much does a Red Oak vacation package cost?
You'll find cheap prices from $368 on Expedia for your Red Oak getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Red Oak costs.
What are the cheapest months to go to Red Oak?
January, October and December are great times to search for cheap Red Oak vacation packages. Traveling in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Red Oak?
Usually, a handful of days is enough to see the major attractions during your Red Oak vacation. But if you prefer to have time to unwind or take day trips, consider extending your itinerary.
How to find the best Red Oak package deals?
Finding a cheap Red Oak package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Red Oak package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Red Oak vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays separately. Better still, you can customize your Red Oak 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 Red Oak?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Red Oak adventure.
How to plan a trip to Red Oak?

  1. Pick your dates: What you'd like to do in Red Oak and your favorite season can help you decide when to travel.
  2. Set your budget: Consider costs such as flights, transportation and food when calculating how much to put aside for your trip to Red Oak. Then, pick a property that fits your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Use our trip planning tool to explore Red Oak: Research every aspect of your trip to Red Oak with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Red Oak, you can figure out the perfect length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to see.
  5. Bundle your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Red Oak vacation package for you.
  6. Add on excursions and experiences: Have a look at our travel guide to find some incredible things to do in Red Oak. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Red Oak vacation packages?
Your Red Oak break is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

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