Middleburg Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Middleburg Vacation Packages
Middleburg Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
₩951,253
₩1,161,718 total
Sep 7 - Sep 8
includes taxes & fees
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
₩638,447
₩727,824 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (452 reviews)
"The location is perfect for walking around Middleburg. Parking is complimentary. The staff was very helpful."
Reviewed on Aug 23, 2026
Goodstone Inn & Restaurant
36205 Snake Hill Road Middleburg VA
₩558,313
₩820,752 total
Aug 27 - Aug 28
includes taxes & 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.
Stay near popular Middleburg attractions
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 Fall Races in October for the quintessential Middleburg horse racing experience.
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.
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.
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.
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?
If you're hoping to book a cheap Middleburg vacation 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 vacation, look at which kind of activities and day tours are available nearby.
Is it worth booking a vacation package to Middleburg?
Middleburg is a good vacation 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 vacation 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 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 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 vacation 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 vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Middleburg vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
