Middleburg Vacations from $622
Book a Hotel + Flight or Car together to unlock savings
Your Middleburg Vacation
Our vacation packages to Middleburg give you countless opportunities to discover new sights, sounds and tastes. And with all the finer details taken care of, you'll be free to enjoy your city break to the fullest. If sightseeing is on your list of things to do during your trip to Middleburg, find your way to popular attractions like Kerr Lake Country Club. Check out Expedia's wide range of travel options and book your dream vacation to Middleburg now.
The Latest Middleburg vacation packages
Price found within the past 48 hours. Click for updated prices.
Landing Apartments - Chapel Hill, NC
$936
per person
Nov 25 - Nov 29
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Raleigh (RDU)
9.2/10 Wonderful! (13 reviews)
The apt was clean and nice. Check in was a hassle. Had trouble getting the access code to get our keys. Took 45 min of back and forth standing in the parking garage. Also had to go down a flight of stairs with all our luggage to get to the elevator. Ice maker not working in apt. Positives. Good location, clean and nice apt with gym and a pool.
Reviewed on Aug 17, 2026
Middleburg Hotel Deals
Baymont by Wyndham Henderson Oxford
400 N Cooper Dr Henderson NC
Fully refundableReserve now, pay when you stay
$82 nightly
$93 total
Oct 4 - Oct 5
Total with taxes and fees
Red Roof Inn PLUS+ Henderson
200 Simmons Street Henderson NC
Fully refundableReserve now, pay when you stay
$75 nightly
$85 total
Sep 24 - Sep 25
Total with taxes and fees
Comfort Inn & Suites Oxford South
1000 Martin Luther King Jr. Ave Oxford NC
Fully refundable
$104 nightly
$117 total
Oct 4 - Oct 5
Total with taxes and fees
8.4/10 Very Good! (694 reviews)
"A great value for the money. Room was spacious, clean and comfortable. King bed was very comfortable. Bathroom was nice and clean. Free breakfast was included and was a nice start to the day. Would definitely book here again."
Reviewed on Sep 12, 2026
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 Middleburg Vacation Packages
Middleburg Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Henderson Indoor Flea Market, Kerr Lake Country Club and McGregor Hall |
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Frequently asked questions
How much does a Middleburg vacation package cost?
You'll find cheap prices from $622 on Expedia for your Middleburg getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Middleburg costs.
What are the cheapest months to go to Middleburg?
You can typically find lower rates and better availability in August, November and December. Check out our cheap Middleburg vacation packages and you could get some great off-season deals.
How many days is enough for Middleburg?
The ideal duration for your Middleburg vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to check out all the major attractions and discover some hidden treasures along the way.
How to find the best Middleburg package deals?
Use Expedia's filters to find some tempting Middleburg package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Middleburg package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middleburg vacation as a package?
You can enjoy significant savings on your next Middleburg break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Middleburg?
If you have your Middleburg vacation dates locked in, book early to snap up some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Middleburg trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.