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.
Stay near popular Middleburg attractions
Glenwood Park
10.0/10 (2 reviews)
Glenwood Park becomes a premier equestrian venue hosting steeplechase races over natural hedges. Bring binoculars to the Virginia Fall Races in October for the quintessential Middleburg horse racing experience.
Red Fox Fine Art
9.6/10 (10 reviews)
America's leading gallery for sporting art, Red Fox Fine Art showcases exquisite 19th and 20th-century paintings and sculptures. Browse the curated collection that celebrates equestrian heritage in an intimate setting.
Greenhill Winery & Vineyards
9.4/10 (28 reviews)
This boutique vineyard showcases 100% Virginia wines in a historic 1762 stone manor. Enjoy guided tastings paired with specialty cheeses and charcuterie while taking in panoramic views of the Middleburg countryside.
Middleburg Historic District
10.0/10 (1 review)
This charming 18th-century town is the undisputed "Nation's Horse and Hunt Capital." Explore boutique shops and galleries, then time your visit for the thrilling Middleburg Spring Races in May.
Chrysalis Vineyards
8.4/10 (9 reviews)
Home to the world's largest planting of Norton grapes, Chrysalis Vineyards offers distinctive wine flights in Virginia's rolling hills. Savor estate wines on the adults-only upper deck with artisanal pizzas.
Cana Vineyards and Winery
7.8/10 (14 reviews)
This 43-acre wine estate offers mountain views and Virginia vintages in a welcoming countryside setting. Savor self-guided flights or weekend tastings paired with authentic Italian gelato and New York-style pizzas.
The Byrne Gallery
10.0/10 (1 review)
You can spend an afternoon exploring the galleries in The Byrne Gallery during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
Middleburg Community Center
This historic nonprofit venue offers elegant spaces and private gardens in the heart of Middleburg. Explore the Grand Ballroom with its soaring 24-foot ceilings or attend one of the community's seasonal events.
What to do in Middleburg
Loudoun County 3-Winery Tour from DC Metro or Leesburg
$120
per adult
Guided Thrift Store Walking Tour in Historic Leesburg
$50
per adult
Middleburg Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
$700 nightly
$798 total
Sep 29 - Sep 30
Total with taxes and fees
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
$436 nightly
$498 total
Sep 27 - Sep 28
Total with taxes and fees
9.6/10 Exceptional! (456 reviews)
"1"
Reviewed on Sep 21, 2026
Goodstone Inn & Restaurant
36205 Snake Hill Road Middleburg VA
$524 nightly
$598 total
Sep 23 - Sep 24
Total with taxes and fees
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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.