Red Oak Vacations from $340

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The Latest Red Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
Price was $429, price is now $340 per person
$340
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
9/10 Wonderful! (3,188 reviews)
The washer was broken, but the dryer worked. I also went to use one of the spare blankets they leave in the closet and once I unfolded it, a bunch of pieces of used up + bloody tissues came out. Other than those two things, it was a pretty nice stay.

Reviewed on Jan 30, 2026

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was $622, price is now $458 per person
$458
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
8.8/10 Excellent! (427 reviews)
The layout of our room was great for a family vacation. The location is ideal for access to Colonial Williamsburg. My daughter loved the kid friendly amenities like the game room, pool and access to board games through the front desk. Most importantly, though, the staff was so welcoming and helpful. Every person we had contact with from house keeping to the front desk treated us with warmth and kindness.

Reviewed on Dec 29, 2025

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $541, price is now $409 per person
$409
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
9.4/10 Exceptional! (310 reviews)
Spacious, clean, except under the night tables beside the bed.

Reviewed on Jan 13, 2026

Wedmore Place

Wedmore Place

3.5 out of 5
Price was $642, price is now $497 per person
$497
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
Beautiful place inside and out!

Reviewed on Feb 3, 2026

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $542, price is now $430 per person
$430
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
8.8/10 Excellent! (1,000 reviews)
The overall room and staff were excellent. I understand the winter strom can effect some activities. Only thing that really bother us was that there was no more treating of the sidewalks. When we checked in the ice melt was down and when we checked out it was all iced over and nothing else had been done since Saturday.

Reviewed on Jan 28, 2026

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Red Oak Hotel Deals

Microtel Inn & Suites by Wyndham South Hill

Microtel Inn & Suites by Wyndham South Hill

2 out of 5
111 Arnold Drive La Crosse VA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from Feb 14 to Feb 15
$108 total
Feb 14 - Feb 15
Total with taxes and fees
9/10 Wonderful! (523 reviews)
My room was really clean. The staff was helpful and accommodating. I had two large dogs with me which wasn’t ideal but it was a last minute thing. There’s a large field and woods right next to the hotel which made walking the dogs so much easier.

Reviewed on Jan 31, 2026

Microtel Inn & Suites by Wyndham South Hill
Comfort Inn & Suites South Hill I-85

Comfort Inn & Suites South Hill I-85

2.5 out of 5
250 Thompson Street South Hill VA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $92 total per night from Mar 1 to Mar 2
$92 total
Mar 1 - Mar 2
Total with taxes and fees
8/10 Very Good! (516 reviews)
Room was excellent

Reviewed on Jan 15, 2026

Comfort Inn & Suites South Hill I-85
Hampton Inn South Hill

Hampton Inn South Hill

2.5 out of 5
200 Thompson Rd South Hill VA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Feb 22 to Feb 23
$109 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (512 reviews)
Perfect stay!

Reviewed on Jan 16, 2026

Hampton Inn South Hill
See all 467 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 $340 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.