Red Oak Vacations from $380

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The Latest Red Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $529, price is now $380 per person
$380
per person
Apr 23 - Apr 28
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
9.6/10 Exceptional! (99 reviews)
We had a great experience staying at Pinball Pete’s place. Very clean, cozy, comfortable, with use of the kitchen and some food provided … and, of course, pinball! Our host also went above and beyond in helping us to resolve an unexpected issue. Hoping to stay there again in the future.

Reviewed on Dec 22, 2025

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 $900, price is now $595 per person
$595
per person
Apr 16 - Apr 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (765 reviews)
Great hotel, bathroom was was out dated

Reviewed on Feb 2, 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 $718, price is now $513 per person
$513
per person
Apr 16 - Apr 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (427 reviews)
Staff was very helpful and friendly. The room was very clean and comfortable. My kids loved the game room and pool! We would absolutely stay here again.

Reviewed on Feb 8, 2026

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $698, price is now $500 per person
$500
per person
Apr 16 - Apr 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $904, price is now $663 per person
$663
per person
Apr 16 - Apr 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
beautiful property and room, will be back!

Reviewed on Feb 17, 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
$91 nightly
The price is $102 total per night from Feb 27 to Feb 28
$102 total
Feb 27 - Feb 28
Total with taxes and fees
8.6/10 Excellent! (212 reviews)
The hotel was all around, perfect. The staff made it especially pleasant. They were very helpful and went the extra mile. The room itself was clean and just what I needed.

Reviewed on Jan 14, 2026

Best Western Plus South Hill Inn
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
$101 nightly
The price is $113 total per night from Mar 13 to Mar 14
$113 total
Mar 13 - Mar 14
Total with taxes and fees
9.2/10 Wonderful! (529 reviews)
For the lower price of this hotel compared to other hotel chains we trust, we were very impressed! We would try to stay here again on this route in the future. Staff was friendly. Check in at 11:30pm was the fastest I’ve ever experienced, because our check-in sheet was already printed for me to sign. ...

Reviewed on Feb 15, 2026

Microtel Inn & Suites by Wyndham South Hill
Inn at Blackstone

Inn at Blackstone

2.5 out of 5
707 4th Street Blackstone VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $136 total per night from Mar 14 to Mar 15
$136 total
Mar 14 - Mar 15
Total with taxes and fees
9.2/10 Wonderful! (316 reviews)
Loved that they refurbished the Women's College! Room was perfect! It was clean and quiet, original hardwoods were beautiful! Staff was so friendly and welcoming. I would recommend the Inn and I will stay there again!

Reviewed on Feb 11, 2026

Inn at Blackstone
See all 466 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 $380 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.