Red Oak Vacations from $369

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The Latest Red Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
The Colonies at Williamsburg

The Colonies at Williamsburg

$369
per person
Dec 4 - Dec 6
found 17 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
9/10 Wonderful! (1,055 reviews)
Kingsmill Resort

Kingsmill Resort

Kingsmill
$601
per person
Dec 10 - Dec 14
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.6/10 Excellent! (1,007 reviews)
We enjoyed the property. We choice the room on expedia website expecting one of the larger room apartment style rooms but we ended up with a smaller hotel room. You have to pay an extra fee if you want a 1 bedroom room. Wasn't fully clear based on pictures. We could hear the other guest at night. Visited the eagle restaurant. Staff were very pleasant and accommodating. The light fixtures outdide above the tables has lots of spider web's. Need to be cleaned. The room was clean. Air conditioner was noisy. Enjoyed our stay otherwise. Gym and pools were great. The pump for the lazy river and hot tubs were not on, but sgaun still enjoyed our stay.

Reviewed on Sep 20, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$474
per person
Dec 10 - Dec 14
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.8/10 Excellent! (1,941 reviews)
Loud neighbors next door kept me up at night. Freezing room, she is

Reviewed on Sep 21, 2026

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

$613
per person
Dec 10 - Dec 14
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.2/10 Wonderful! (262 reviews)
I rented two, two-bedroom units (condominiums). The units were large and nicely appointed. Kitchen was well equipped. Very pleased with the facility.

Reviewed on Sep 21, 2026

Patriots Inn

Patriots Inn

$419
per person
Dec 10 - Dec 14
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.4/10 Exceptional! (1,071 reviews)
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Red Oak Hotel Deals

Inn at Blackstone

Inn at Blackstone

707 4th Street Blackstone VA
Fully refundableReserve now, pay when you stay
$82 nightly
$91 total
Oct 9 - Oct 10
Total with taxes and fees
9.2/10 Wonderful! (412 reviews)
"What a wonderful surprise! Definitely will be back!!!"

Reviewed on Sep 16, 2026

Inn at Blackstone
Best Western Plus South Hill Inn

Best Western Plus South Hill Inn

101 Thompson St La Crosse VA
Fully refundableReserve now, pay when you stay
$101 nightly
$113 total
Oct 4 - Oct 5
Total with taxes and fees
8.8/10 Excellent! (287 reviews)
"The rooms were clean. Staff were helpful and cheerful. It was nice that they did not have carpet. The coffee machine that freshly grinds and makes a variety of drinks was a plus. No frills, but very functional."

Reviewed on Sep 18, 2026

Best Western Plus South Hill Inn
Crewe Boutique Inn

Crewe Boutique Inn

16092 W Colonial Trail Hwy Crewe VA
Fully refundableReserve now, pay when you stay
$73 nightly
$81 total
Oct 22 - Oct 23
Total with taxes and fees
Crewe Boutique Inn
See all 496 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 $369 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.

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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.