Middleburg Packages (Flight + Hotel)

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Top hotels in Middleburg

Salamander Resort And Spa
Salamander Resort And Spa
5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is ฿20,126 per night from 30 Jun to 1 Jul
฿20,126
฿24,644 total
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (356 reviews)
"We were most impressed about the outstanding friendliness and hospitality of the staff. Felt like in a Japanese Ryokan where the guest is king. One hick-up with the restaurant at the first night, which was charmingly fixed by the management."

Reviewed on 20 Jun 2025

Salamander Resort And Spa
The Red Fox Inn & Tavern
The Red Fox Inn & Tavern
4 out of 5
2 E Washington St, Middleburg, VA
9.6/10 Exceptional! (364 reviews)
"Love Red Fox Inn! My go to spot in Middleburg!"

Reviewed on 20 Jun 2025

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The Red Fox Inn & Tavern
Hyatt Regency Dulles
Hyatt Regency Dulles
4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
The price is ฿3,588 per night from 4 Jul to 5 Jul
฿3,588
฿4,055 total
4 Jul - 5 Jul
includes taxes & fees
8.8/10 Excellent! (1,300 reviews)
"Stayed for one night and it was great. Very nice staff members"

Reviewed on 19 Jun 2025

Hyatt Regency Dulles
See all 961 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?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Middleburg costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Middleburg?
If you're hoping to book a cheap Middleburg holiday package, consider visiting in January, April and September. You'll usually find lower prices on hotels and flights during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Middleburg?
You can visit all the main attractions in Middleburg within a few days, including the must-see Chrysalis Vineyards. If you're after a longer Middleburg holiday, look at which kind of activities and day tours are available nearby.
Is it worth booking a holiday package to Middleburg?
Middleburg is a good holiday destination with attractions like Glenwood Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Middleburg holiday promises a good time for everyone.
How to find the best Middleburg package deals?
Use Expedia's filters to help you find some tempting Middleburg package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Middleburg package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Middleburg holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can personalise your Middleburg getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Middleburg?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Middleburg escape.
How to plan a trip to Middleburg?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to holiday in Middleburg.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to Middleburg. Then, choose a property that suits your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide how long to go away for: Now that you know more about Middleburg, you can figure out the perfect length of your holiday. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the right Middleburg holiday package for you.

What to do in Middleburg

Vineyard and Winery Bus Tour from Metro DC

Vineyard and Winery Bus Tour from Metro DC

฿3,564
per adult
Vineyard and Winery Bus Tour from Metro DC
Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

฿2,916
per adult
Leesburg Premium Outlets Shopping Tour
Celebrate with a winery tour to some of Virginia's best wineries and vineyards by Spirited Tours.

Private Washington DC Virginia Winery Wine Tasting Tour -Spirited

฿8,263
per adult
Private Washington DC Virginia Winery Wine Tasting Tour -Spirited
See all activities in Middleburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.