Middleburg Holidays
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Top hotels in Middleburg
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
Rp9.422.770
Rp11.741.685 total
3 Sept - 4 Sept
includes taxes & fees
9.2/10 Wonderful! (410 reviews)
"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"
Reviewed on 21 Jul 2026
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
Rp7.255.444
Rp8.271.099 total
9 Aug - 10 Aug
includes taxes & fees
Hyatt Regency Dulles International Airport
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
Rp2.205.805
Rp2.536.675 total
22 Aug - 23 Aug
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
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.
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.
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.
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.
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.
What to do in Middleburg
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Rp2.167.619
per adult
Virginia Wineries Guided Tour and Tastings from Washington DC
Rp4.154.950
per adult
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?
- 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.
