Discover the most popular places to visit in Middleburg
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.
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 Autumn Races in October for the quintessential Middleburg horse racing experience.
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. Savour 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. Savour self-guided flights or weekend tastings paired with authentic Italian gelato and New York-style pizzas.
National Sporting Library & Museum
9.8/10 (8 reviews)
This unique museum celebrates America's equestrian heritage through rare sporting art and literature. Browse horse and hound paintings and explore rare books in the historic Vine Hill mansion.
Museum of Hounds & Hunting North America
2.0/10 (1 review)
This intimate museum preserves America's foxhunting heritage through art and artefacts dating back generations. View historic paintings, examine hunting horns, and learn about the cultural traditions of the hunt country.
The Byrne Gallery
10.0/10 (1 review)
You can spend an afternoon studying the exhibits at The Byrne Gallery during your trip to Middleburg. Visit the area's spas or simply enjoy its restaurants.
"We stayed in the main building. We were on the 3rd floor. The hall ways are warm but the rooms were very cool- good ac. Breakfast was easy, plentiful and food. Staff was helpful when needed. There appears to be some renovations , but it didn’t effect our stay."
"Kara was rude upon questioning why my card was charged prior to arrival. Room smelled like mildew. No coffee at breakfast...jug empty at 9am. Overall bad experience, definitely will seek other options next time around."
"Great location. Staff is very nice. A short walk to the casino/races. Shuttle is available but we’ve never used it. We’ve stayed here multiple times-always a great experience."
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.
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.
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?
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.
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.
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.
Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the right 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.