Middleburg Vacations from $484

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 Middleburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Brunswick near Frederick

Travelodge by Wyndham Brunswick near Frederick

2 out of 5
Price was $514, price is now $484 per person
$484
per person
Jul 1 - Jul 4
found 23 hours ago
Roundtrip flight included
Las Vegas (LAS) to Hagerstown (HGR)
9.2/10 Wonderful! (376 reviews)
The staff was very helpful and friendly. Rooms and bathrooms were clean and the bed felt great!

Reviewed on Feb 2, 2026

SureStay Plus Hotel by Best Western Berkeley Springs

SureStay Plus Hotel by Best Western Berkeley Springs

2.5 out of 5
Price was $802, price is now $762 per person
$762
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Hagerstown (HGR)
8.6/10 Excellent! (975 reviews)
It smelled like old shoes!

Reviewed on May 3, 2026

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

Middleburg Hotel Deals

Wyndham Gettysburg Hotel & Conference Center

Wyndham Gettysburg Hotel & Conference Center

3.5 out of 5
95 Presidential Cir Gettysburg PA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $122 total per night from May 10 to May 11
$122 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,558 reviews)
Beautiful place, amazing collection of memorabilia. Restaurant was excellent with great service. I would definitely stay there again if in the area.

Reviewed on May 3, 2026

Wyndham Gettysburg Hotel & Conference Center
Hotel Gettysburg

Hotel Gettysburg

4 out of 5
One Lincoln Square Gettysburg PA
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $163 total per night from May 21 to May 22
$163 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (1,276 reviews)
No

Reviewed on May 6, 2026

Hotel Gettysburg
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $153 total per night from May 10 to May 11
$153 total
May 10 - May 11
Total with taxes and fees
9.4/10 Exceptional! (1,013 reviews)
The food was average breakfast fare but the breakfast room was outside of our bedroom in a hallway on the second floor. The weirdest setup we’ve ever seen. The woman who prepared everything was wonderful. Otherwise, we were comfortable there.

Reviewed on May 6, 2026

Inn at Cemetery Hill
See all 372 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

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 Middleburg vacation package cost?
Offering excellent value package deals from $484 on Expedia, you'll be surprised at how little a vacation to Middleburg costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middleburg?
If you're hoping to snag a cheap Middleburg vacation package, consider traveling in December, January and February. You'll usually find better prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Middleburg?
Usually, a handful of days is enough to check out the major sights during your Middleburg vacation. But if you want to have time to unwind or take day tours, think about extending your itinerary.
How to find the best Middleburg package deals?
Use Expedia's filters to help you find some great Middleburg package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Middleburg package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Middleburg vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a customized Middleburg vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Middleburg?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Middleburg trip.
Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
Jet off on your dream escape to Middleburg with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.