Middleburg Vacations from $288

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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.
Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was $402, price is now $288 per person
$288
per person
Nov 21 - Nov 24
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.8/10 Excellent! (907 reviews)
Clean hotel, nice breakfast and convenient location

Reviewed on Sep 3, 2025

Rizzo Center, a Destination by Hyatt Hotel

Rizzo Center, a Destination by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $552, price is now $374 per person
$374
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
9.6/10 Exceptional! (1,003 reviews)
I really enjoyed this property. Each floor has an area with snacks in a refrigerator like sodas and ice cream and popcorn. We stayed during a not very busy time, but I bet this place would be amazing during a football or basketball game.

Reviewed on Sep 4, 2025

Homewood Suites by Hilton Raleigh/Cary

Homewood Suites by Hilton Raleigh/Cary

3 out of 5
Price was $608, price is now $450 per person
$450
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Raleigh (RDU)
8.8/10 Excellent! (913 reviews)
Everyone was excellent and friendly towards me Especially Tanya!

Reviewed on Jul 29, 2025

Graduate by Hilton Chapel Hill

Graduate by Hilton Chapel Hill

4 out of 5
Price was $584, price is now $444 per person
$444
per person
Nov 16 - Nov 19
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.2/10 Wonderful! (1,003 reviews)
It sure is a uniquely themed and relatively small hotel, with basketball themed hardwoods, and headboards on each bed. The staff are great and the bar area is particularly nice. Facilities are limited and breakfast is not included. The building infrastructure Needs a little work as the AC unit was incredibly Loud, the loudest of any hotel I’ve ever stayed at and the concrete on the balcony was crumbling. I do think that the hotel was overpriced for the services on offer but you can’t beat the location.

Reviewed on Aug 31, 2025

Wingate by Wyndham State Arena Raleigh/Cary

Wingate by Wyndham State Arena Raleigh/Cary

3 out of 5
Southwest Raleigh
Price was $442, price is now $337 per person
$337
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,012 reviews)
I booked the my stay for a birthday surprise for my young child. We saw pictures of a pool, but found out the hotel did not have a pool for over a year. Then there was active construction the hotel that we were not aware of. The breakfast bar was minimal and had minimal options for my family member with food allergies.

Reviewed on Sep 2, 2025

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Middleburg Hotel Deals

Red Roof PLUS+ Henderson

Red Roof PLUS+ Henderson

2.5 out of 5
200 Simmons Street, Henderson, NC
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $75 total per night from Oct 5 to Oct 6
$75 total
Oct 5 - Oct 6
Total with taxes and fees
Red Roof PLUS+ Henderson
Hampton Inn Henderson

Hampton Inn Henderson

2.5 out of 5
385 Ruin Creek Rd, Henderson, NC
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Sep 28 to Sep 29
$133 total
Sep 28 - Sep 29
Total with taxes and fees
Hampton Inn Henderson
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 Sep 21 to Sep 22
$96 total
Sep 21 - Sep 22
Total with taxes and fees
Baymont by Wyndham Henderson Oxford
See all 249 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.

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Frequently asked questions

How much does a Middleburg vacation package cost?
You'll find cheap prices from $288 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.