Middleburg Vacations from $499

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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.
Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Downtown Raleigh
Price was $630, price is now $499 per person
$499
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.4/10 Exceptional! (1,017 reviews)
Room 217 was too noisy. We could barely sleep with road traffic and construction going on.

Reviewed on Jul 29, 2026

Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Save 100% on your flight
Price was $944, price is now $723 per person
$723
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
No reviews

The Laurel Hotel

The Laurel Hotel

2 out of 5
Price was $690, price is now $531 per person
$531
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.8/10 Exceptional! (106 reviews)

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Price was $826, price is now $645 per person
$645
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
No reviews

Millennium Hotel Durham

Millennium Hotel Durham

3 out of 5
Price was $756, price is now $607 per person
$607
per person
Oct 4 - Oct 9
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
7.4/10 Good! (1,036 reviews)

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Middleburg Hotel Deals

Baymont by Wyndham Henderson Oxford

Baymont by Wyndham Henderson Oxford

2.5 out of 5
400 N Cooper Dr Henderson NC
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $96 total per night from Aug 9 to Aug 10
$96 total
Aug 9 - Aug 10
Total with taxes and fees
7.8/10 Good! (791 reviews)
"The room was clean when I walked in I could smell bleach/ cleaning products. I like that clean smell. The only problem I had is the leaky toilet in or bathroom. Also, I was a little concerned about the sign in the parking lot that said that the hotel is not responsible for your car if it is vandalized ..."

Reviewed on Jul 29, 2026

Baymont by Wyndham Henderson Oxford
Red Roof Inn PLUS+ Henderson

Red Roof Inn PLUS+ Henderson

2.5 out of 5
200 Simmons Street Henderson NC
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $86 total per night from Aug 9 to Aug 10
$86 total
Aug 9 - Aug 10
Total with taxes and fees
7.4/10 Good! (778 reviews)
"Our air died late in the evening during the heatwave sweeping across the area. We have stayed in Red Roof Inns across the nation. Not all Red Roof Inn’s are created equal. This property is in desperate need of repairs…the front door was falling off. There was a smell in the room and the rug felt ..."

Reviewed on Jul 28, 2026

Red Roof Inn PLUS+ Henderson
Comfort Inn & Suites Oxford South

Comfort Inn & Suites Oxford South

2.5 out of 5
1000 Martin Luther King Jr. Ave Oxford NC
Fully refundable
$105 nightly
The price is $119 total per night from Aug 9 to Aug 10
$119 total
Aug 9 - Aug 10
Total with taxes and fees
Comfort Inn & Suites Oxford South
See all 287 properties in Middleburg
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 $499 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.