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
Middleburg Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
$737 nightly
$840 total
Nov 4 - Nov 5
Total with taxes and fees
9.2/10 Wonderful! (423 reviews)
"We love the salamander but the facilities are getting a bit worn down."
Reviewed on Oct 4, 2026
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
$436 nightly
$498 total
Oct 11 - Oct 12
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
$385 nightly
$439 total
Nov 4 - Nov 5
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
What's the best vacation package for Middleburg?
For a romantic Middleburg vacation package, consider a stay at the 4-star Goodstone Inn & Restaurant, rated 9.4 out of 10. This property, about 2 miles from central Middleburg, offers a hot tub, outdoor pool, and a bar/lounge, with travelers frequently praising its beautiful facilities and delicious food.If you're seeking a luxury Middleburg vacation package, the 5-star Salamander Resort And Spa, rated 9.1 out of 10, is an excellent choice. Located about a 10-minute walk from central Middleburg, it features a spa, indoor and outdoor pools, and a bar/lounge, with guests often describing their overall stay as perfect and highlight the lovely facilities.Families looking for the best vacation packages in Middleburg can also find a great option at Salamander Resort And Spa. This resort offers family rooms, a game room, and both indoor and outdoor pools, making it well-suited for all ages, and travelers frequently note the spacious rooms and delicious breakfast.
How can I save money on a Middleburg vacation package?
When you bundle, you can save up to 30%*. To save money on a Middleburg package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Middleburg?
Middleburg, a charming outdoor and nature destination, offers a variety of activities for your Middleburg vacation:Browse and book things to do in Middleburg on Expedia.
Do you need to rent a car in Middleburg, or is public transport enough?
For Middleburg vacation packages with flights, a rental car is highly recommended for exploring this outdoor and nature destination. Middleburg is primarily served by U.S. Route 50, which connects it to other towns and attractions, making a car the most flexible option for reaching sights spread across the area.While some hotels, like the 5-star Salamander Resort And Spa and the 4-star Goodstone Inn & Restaurant, offer airport shuttle services to and from Washington, DC (DCA-Ronald Reagan Washington National) and Washington Dulles Intl. (IAD), having your own vehicle allows for independent day trips to places like Harpers Ferry National Historical Park or the various vineyards.
Are Middleburg vacation package hotels conveniently located?
Middleburg vacation package hotels offer convenient access to the town's attractions, with many properties located within easy reach of central Middleburg.Salamander Resort And Spa, a 5-star property rated 9.1 out of 10, is about a 10-minute walk from central Middleburg, offering spacious rooms and lovely facilities, praised by travelers for its perfect overall experience. The Red Fox Inn & Tavern is about a 5-minute walk from central Middleburg, with guests highlighting its great location and beautiful rooms. For a stay slightly outside the immediate center, Goodstone Inn & Restaurant, a 4-star inn rated 9.4 out of 10, is located about 2 miles from central Middleburg and is noted for its beautiful facilities and attentive staff.Choosing a package hotel in Middleburg means you'll be well-situated to explore the area's charm and natural beauty.
Can I change or cancel my Middleburg vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Middleburg vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Middleburg vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Middleburg?
To find last-minute vacation packages to Middleburg, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Middleburg vacation packages?
Free cancellation on a Middleburg vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Middleburg vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Middleburg getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Middleburg vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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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.
