Middleburg Holidays
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Your Middleburg Holiday
With every last detail planned before you go away, our Middleburg holiday packages mean you can focus more on letting the good times roll. Whether you stay in the neighbourhood 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 holiday on Expedia.
Middleburg Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Washington Dulles Intl. Airport (IAD) |
Population | 810 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Bluemont Vineyard, Greenhill Winery & Vineyards and Quattro Goombas Winery |
Top hotels in Middleburg
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
£616
7 Sept - 8 Sept
includes taxes & fees
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
£386
16 Sept - 17 Sept
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 23 Aug 2026
Goodstone Inn & Restaurant
36205 Snake Hill Road Middleburg VA
£436
27 Aug - 28 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
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.
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 speciality 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. 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.
What to do in Middleburg
Guided Thrift Store Walking Tour in Historic Leesburg
£38
per traveller
Frequently asked questions
Why should I book my Middleburg holiday with Expedia?
Expedia has you covered for all aspects of your next Middleburg trip. You'll always get the best prices around, but when you bundle your accommodation, airfares and/or hire car into a holiday package, you can save even more. Keen to really make the most of your adventure? Add some fun activities and tours to your customised package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to stress if you have to change your plans. Head over to our Customer Service Portal link to find out more.
When is the best time of year to holiday in Middleburg?
Love sightseeing but don't like queuing up for attractions? Plan your Middleburg getaway for March, November and December. Typically, it's much quieter than it is in February, June and August. To give you an idea of the type of weather you can experience, the daytime average temperature in January, the coolest time of year in Middleburg, is 0ºC. The warmest time here is July, when temperatures are around 25ºC.
What is the top hotel for my holiday in Middleburg?
Put your feet up and relax in comfort in Middleburg by choosing Washington Dulles Airport Marriott as your gateway to fun and adventure.
How do I get a cheap holiday to Middleburg?
Booking a flight and hotel together with Expedia won't just save precious time — it'll save you pounds too. A Middleburg holiday makes it a cinch to put together your ideal trip. With more than 400 airlines worldwide to select from, finding flights that fit your busy schedule won't be hard. Not only that, we have over 321,000 hotels globally to choose from. Now that's what we call choice. No matter who you are, Expedia puts the world within your reach. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Middleburg holiday?
With must-see tourist attractions like Greenhill Winery & Vineyards and Cana Vineyards and Winery, a holiday in Middleburg is packed with fun places to visit. Chrysalis Vineyards and Glenwood Park are a couple of other sights also worth a look.
What is the best area to stay in when on holiday in Middleburg?
An escape to Middleburg wouldn't be complete without checking out Greenhill Winery & Vineyards. Why not stay near this much-loved tourist attraction?
Do I need a visa for my Middleburg holiday?
Check the latest rules on official government websites. Your nationality and whether you're travelling for business, study or leisure will determine if you'll require a visa for Middleburg. Make yourself familiar with the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow sufficient processing time. Some visas may take weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Middleburg holiday?
Though everyone's style differs, it can help to have some guidelines for what type of clothes to wear on your holiday in Middleburg. We recommend searching style blogs before leaving for inspiration on local fashion trends. Check the weather forecast so you can pack your bags accordingly. The warmest month in Middleburg is July, with average daytime temperatures of 25ºC. If you're travelling in the coolest month of January, the mercury hovers around 0ºC during the day.
What does an Expedia Middleburg holiday include?
With Expedia, you can choose a combination of flights, car hires and hotels to create your perfect Middleburg travel package. Once you've made your booking, simply add on the fun stuff like tours and experiences. Don't forget, the more you bundle, the greater the savings! Private holiday homes and cottages are two of the most highly sought-after property types in Middleburg. No matter your holiday style or size of your group, you can count on Expedia for the freedom and flexibility to customise your escape.
Does Expedia offer Book Now, Pay Later Middleburg holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book your dream getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in several transactions will make that dream getaway possible.
- No-deposit holidays: When you want to grab an unbeatable deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.
Can I choose my airline with a Middleburg Expedia holiday?
You can, and with more than 400 airlines to choose from throughout the world, you have plenty of choice. Take a look at the available options and find out which airline best suits your budget and needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
