Red Oak Vacations from $478

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Red Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

3 out of 5
Price was $669, price is now $478 per person
$478
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9/10 Wonderful! (1,005 reviews)
Hot tub and vending machines have been removed. Dinner menu is extremely minimal. Staff was friendly and room was clean.

Reviewed on May 1, 2026

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $944, price is now $586 per person
$586
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.6/10 Excellent! (1,002 reviews)
We got a great deal on this property through Expedia and were very happy with the property. It’s feel like historic Williamsburg with great location close to William & Mary and shops/restaurants on Richmond Hwy. The staff was super friendly and while the room was in older side - it was clean and worked fine for our 2 night stay. I was bummed not to use outdoor pool and hot tub (a little chilly - early May stay) but my husband and I enjoyed playing mini golf. I would recommend this hotel/resort!!

Reviewed on May 3, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $771, price is now $539 per person
$539
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (806 reviews)
Wonderful stay. The only difficulty would be finding the building at night. Poor lighting of the surrounding property. But the staff in the main building was very helpful and addressed the problem immediately.

Reviewed on Apr 27, 2026

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Save 100% on your flight
Price was $1,132, price is now $816 per person
$816
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.2/10 Wonderful! (249 reviews)
Wonderful experience once again. Indoor pool was ice cold due to a broken thermostat. Hopefully it will be fixed when we return.

Reviewed on May 5, 2026

Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $1,026, price is now $741 per person
$741
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,008 reviews)
Beautiful grounds, super friendly staff, nice selection for breakfast. Just an all around beautiful place to stay and enjoy everything that the area has to offer

Reviewed on May 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to Red Oak
View all trips

Red Oak Hotel Deals

Inn at Blackstone

Inn at Blackstone

2.5 out of 5
707 4th Street Blackstone VA
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $138 total per night from May 18 to May 19
$138 total
May 18 - May 19
Total with taxes and fees
9.2/10 Wonderful! (343 reviews)
Great place - best stay in Blackstone

Reviewed on May 8, 2026

Inn at Blackstone
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
$98 nightly
The price is $110 total per night from May 17 to May 18
$110 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (238 reviews)
Very friendly staff. Breakfast was good

Reviewed on May 8, 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
$80 nightly
The price is $89 total per night from May 10 to May 11
$89 total
May 10 - May 11
Total with taxes and fees
8.6/10 Excellent! (179 reviews)
Really nice and helpful staff. Room was very clean, quiet and comfortable. Breakfast was one of the best complimentary breakfasts out there. Not much close by, but there's a restaurant on the property.

Reviewed on Apr 30, 2026

Crewe Boutique Inn
See all 469 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)

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Red Oak vacation package cost?
You'll find cheap prices from $478 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.