Middleburg Vacations

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Your Middleburg Vacation

With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.

Discover the most popular places to visit in Middleburg

Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

Glenwood Park

5/5(1 review)

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Glenwood Park
Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Red Fox Fine Art

Greenhill Winery & Vineyards

3.5/5(3 reviews)

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this relaxing area.

Greenhill Winery & Vineyards

What to do in Middleburg

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

$90
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

$120
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
See all activities in Middleburg

Middleburg Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
$693 nightly
The price is $790 total per night from Jun 23 to Jun 24
$790 total
Jun 23 - Jun 24
Total with taxes and fees
9.2/10 Wonderful! (398 reviews)
"Beautiful stay all around!"

Reviewed on May 29, 2026

Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
$446 nightly
The price is $509 total per night from Jun 12 to Jun 13
$509 total
Jun 12 - Jun 13
Total with taxes and fees
9.6/10 Exceptional! (436 reviews)
"Very nice and unique Inn going back to 1700+"

Reviewed on May 28, 2026

The Red Fox Inn & Tavern
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Jun 20 to Jun 21
$126 total
Jun 20 - Jun 21
Total with taxes and fees
8.8/10 Excellent! (1,765 reviews)
"This Hyatt is good for travelers. It is easy to get to and restaurants and shopping or close by. They have an airport shuttle that runs around the clock. You can leave your vehicle on site for a daily rate. Bed was comfortable, room had plenty of space, there is a restaurant and bar on site. We did ..."

Reviewed on Jun 8, 2026

Hyatt Regency Dulles International Airport
See all 994 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
Closest Airport
Washington Dulles Intl. Airport (IAD)
Population
810
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Greenhill Winery & Vineyards, Chrysalis Vineyards and Cana Vineyards and Winery

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Frequently asked questions

How much does a Middleburg vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation 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?
You're likely to find lower rates and greater availability in March, November and December. Check out our cheap Middleburg vacation packages and you could get some excellent off-season deals.
How many days is enough for Middleburg?
Typically, a few days is great for a Middleburg vacation. With a well-planned itinerary, you can go to all the leading attractions including Chrysalis Vineyards, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Middleburg?
Middleburg offers everything you need for an unforgettable getaway. Begin your Middleburg vacation on a high note by visiting top attractions like Glenwood Park.
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 vacation package as early as possible.
Is it cheaper to book a Middleburg vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can personalize 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 vacation 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 get away: Check your schedule and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to vacation in Middleburg.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Middleburg.
  3. Use Expedia's trip planning tool to explore Middleburg: Research every aspect of your trip to Middleburg with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend exploring Middleburg. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Middleburg vacation package.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on Middleburg's best offerings. Find all the incredible things to do in Middleburg with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
Jet off on your dream getaway to Middleburg with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snap up travel deals while they last.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.