Middleburg Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Middleburg

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
The price is S$144 per night from 31 Aug to 1 Sept
S$144
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,480 reviews)
"Pool times were amazing very clean and comfortable and everyone was kind"

Reviewed on 16 Aug, 2025

Wyndham Gettysburg Hotel & Conference Center
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is S$120 per night from 24 Aug to 25 Aug
S$120
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,081 reviews)
"It was ok for the price"

Reviewed on 15 Aug, 2025

Country Inn & Suites by Radisson, Frederick, MD
Days Inn by Wyndham Gettysburg

Days Inn by Wyndham Gettysburg

3 out of 5
865 York Rd, Gettysburg, PA
Fully refundableReserve now, pay when you stay
The price is S$100 per night from 31 Aug to 1 Sept
S$100
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,107 reviews)
"The facility is clean, quiet, centrally located and affordably priced. Check in and out were quick and easy, I will recommend this for anyone visiting the area!"

Reviewed on 13 Aug, 2025

Days Inn by Wyndham Gettysburg
See all 335 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.

Frequently asked questions

How much does a Middleburg holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Middleburg costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middleburg?
You can generally find lower prices and greater availability in January, February and March. Check out our cheap Middleburg holiday packages and you could get some great off-season discounts.
How many days is enough for Middleburg?
Generally, a handful of days is enough to go to the main attractions during your Middleburg holiday. However, if you prefer to have some time to relax or go on day tours, think about extending your trip.
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 holiday package as early as possible.
Is it cheaper to book a Middleburg holiday as a package?
Expedia holiday 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 customised Middleburg holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Middleburg?

  1. Pick your dates: The things you plan to do in Middleburg and your favourite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Middleburg.
  3. Decide your trip length: Think about how long you want to spend discovering Middleburg. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, book the perfect Middleburg holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.