Middleburg, VA

Travel Guide

A sunrise over a mountainous landscape with layers of clouds.
A sunset over a snow-covered landscape with bare trees and a clear sky.
A street with parked cars and storefronts, including a jewelry store and a restaurant.
A group of dogs standing on grass, with a horse in the background.
A group of hounds on a grassy field with a horse and rider in the foreground.

Where to stay in Middleburg

Find the best Middleburg areas and neighborhoods for the activities you enjoy most. Learn more about Middleburg
Learn more about Middleburg

Downtown

While visiting Downtown, you might make a stop by sights like Middleburg Historic District and Red Fox Fine Art.

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundable
$700 nightly
The price is $798 total per night from Sep 29 to Sep 30
$798 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
$436 nightly
The price is $498 total per night from Sep 27 to Sep 28
$498 total
Sep 27 - Sep 28
Total with taxes and fees
Stay at this inn in Middleburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Red ...
9.6/10 Exceptional! (456 reviews)
"1"

Reviewed on Sep 21, 2026

The Red Fox Inn & Tavern
Goodstone Inn & Restaurant

Goodstone Inn & Restaurant

4 out of 5
36205 Snake Hill Road Middleburg VA
$524 nightly
The price is $598 total per night from Sep 23 to Sep 24
$598 total
Sep 23 - Sep 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Middleburg. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions Glenwood Park and Middleburg ...
Goodstone Inn & Restaurant
See all 1,016 properties in Middleburg
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.
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
Stay at this cottage in Middleburg. Enjoy free WiFi, a garden, and patios. Popular attractions The Boxwood Winery and Middleburg Community Center are located ...
10/10 Exceptional! (66 reviews)
"Great stay! Would definitely visit again."

Reviewed on Sep 6, 2026

18th Century Stone Cottage minutes from historic Middleburg
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

Middleburg VA
Stay at this vacation home in Middleburg. Enjoy laundry facilities and air conditioning. Popular attractions Glenwood Park and Middleburg Community Center are ...
10/10 Exceptional! (2 reviews)
"Loved the nice touches like extra towels on the bed with little chocolates, water and other drinks in the refrigerator, everything you need to make coffee or tea, etc. Also, met the owner who was super friendly and helpful. Would definitely want to stay here again!"

Reviewed on Jan 29, 2026

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Global Luxury Suites at Town Center

Global Luxury Suites at Town Center

4 out of 5
12000 Inspiration St Reston VA
Stay at this apartment in Reston. Enjoy an outdoor pool, a 24-hour fitness center, and parking (surcharge). Popular attractions ArtInsights Animation and Film ...
8.4/10 Very Good! (23 reviews)
"Checks most boxes."

Reviewed on Sep 11, 2026

Global Luxury Suites at Town Center
See all properties in Middleburg
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

A waterfall, a river, and a house in the background.

Glenwood Park

10.0/10 (2 reviews)
Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
See properties

Things to do

Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

Loudoun County 3-Winery Tour from DC Metro or Leesburg

$120
per adult
Loudoun County 3-Winery Tour from DC Metro or Leesburg
Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

$100
per adult
Leesburg Premium Outlets Shopping Tour
Guided Thrift Store Walking Tour in Historic Leesburg

Guided Thrift Store Walking Tour in Historic Leesburg

$50
per adult
Guided Thrift Store Walking Tour in Historic Leesburg
See all activities in Middleburg

Frequently asked questions

Is Middleburg worth visiting?
Middleburg is worth visiting for its rich history, which travelers can explore in the Middleburg Historic District. You can also visit Greenhill Winery & Vineyards and discover the distinct Downtown area. The destination also offers a variety of North American and Italian dining options.
When is the best time to visit Middleburg?
The best time to visit Middleburg is from May through September, when the weather is typically warm and inviting. For travelers seeking fewer crowds and better value, the quieter months of November through February are a good option, offering a cooler experience.
Where are the best neighborhoods to explore in Middleburg?
The best neighborhoods to explore in Middleburg depend on what you want to see:

  • Downtown offers a variety of experiences, including the Tudor Day Spa, Red Fox Fine Art, and The Byrne Gallery.

What is Middleburg known for?
Middleburg is known for its historic charm, featuring the Middleburg Historic District and specific places like Greenhill Winery & Vineyards. Travelers can also explore art at Red Fox Fine Art. The destination offers a taste of North American food culture, especially in areas like Downtown.
What is a good itinerary length for Middleburg?
A good itinerary length for Middleburg is one to two days to explore the Middleburg Historic District, visit Downtown, and see Red Fox Fine Art. An extended stay of three to four days allows more time to enjoy Greenhill Winery & Vineyards and sample the local North American, Italian, and Asian dining options.
What are the top things to do in and around Middleburg?
Middleburg offers a mix of historic charm, art, and natural beauty for travelers to enjoy:


What cuisines can you find in Middleburg?
In Middleburg you can find Thai cuisine, with dishes like Pad Thai, Green Curry, and Tom Yum Soup. Travelers also have options for North American, Italian, Japanese, Chinese, and Mexican dishes. You can also enjoy local coffee shops and wine lounges.
Can I book a refundable hotel in Middleburg?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middleburg by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middleburg with Expedia?
Expedia makes it easier to plan your Middleburg trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middleburg?
The best choice depends on your travel style. Hotels in Middleburg can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middleburg trip on Expedia?
Once you've booked your Middleburg trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middleburg trip?
Expedia offers customer support before, during, and after your Middleburg trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middleburg?
If it's your first trip to Middleburg, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middleburg hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middleburg hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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