Middleburg

Travel Guide

central street of the ancient town near Washington. Ancient buildings of shops, hotels and restaurants., strolling tourists.
Middleburg, VA is a beautiful and sweet little town. During the first weekend of December, the town celebrates the holidays with a parade of horses and hounds, ready for the fox hunt; performances from area schools; even more horses; and all the corgis you could ever need. While I was only a visitor, I felt like I was a part of the small town joy and excitement for the holiday. This is certainly something I'll go back to! #virginia #parades #holidays
A quiet town that is one fourth quaint, one fourth stuck in the past, one fourth high society, and one fourth English countryside. Housing less than a thousand residents (as of the 2000 census), Middleburg is a tiny blip of a town with a lot of character. Stroll the streets and look at the old buildings, stop into shops that sell pricy materials, and look at the devotion to horse and hunt. The town was established shortly after the American Revolution and that old-time feel is still there. Plus, fox hunting! I have never been to a place that does fox hunting and the clean, precise clothes can be purchased at local shops.
This winery is fairly new. I think they need a few more years to establish their wine selection. However the wines weren't terrible. I've just had better in this area. But the view from the upper deck is amazing. Definitely worth checking out if you are in the area. Staff is very friendly and knowledgeable. And their sangria was great! #drinkvirginiawine #winesnob #virginia #winery #canavineyard #outdoors
An terrific surprise find on a day of antiquing and vineyard stops. Leaves of Grass is wonderful. A beautiful tasting room in converted barn, great views, and amazing owner hosts. Only 4 wines right now but they are darn good. A long winding driveway right off Rt 50 and a little hard to find so go up driveway at 39060 john mosby (50) hwy. Love this place

Where to stay in Middleburg

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Downtown

If you're spending some time in Downtown, Middleburg Historic District and Red Fox Fine Art are top sights worth seeing.

Downtown
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
The price is RM2,264 per night from 5 Apr to 6 Apr
RM2,264
RM2,785 total
5 Apr - 6 Apr
includes taxes & fees
Stay at this luxury resort in Middleburg. Enjoy free Wi-Fi, an outdoor pool and a full-service spa. Popular attractions Middleburg Community Center and Red Fox ...
9.2/10 Wonderful! (385 reviews)
The spa treatments are amazing. In addition, the restaurant is excellent at making simple dish extra special. I highly recommend the avocado toast from the breakfast menu.

Reviewed on 18 Mar 2026

Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
Stay at this inn in Middleburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (427 reviews)
Convenient parking, quiet room, would stay again.

Reviewed on 16 Mar 2026

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The Red Fox Inn & Tavern
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
The price is RM398 per night from 3 Apr to 4 Apr
RM398
RM458 total
3 Apr - 4 Apr
includes taxes & fees
Stay at this golf hotel in Hunter Mill. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,649 reviews)
All was fine but when I arrived they charged me about $50 more than the Hotels.com quote

Reviewed on 18 Mar 2026

Hyatt Regency Dulles International Airport
See all 981 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.
Global Luxury Suites at Reston Town Center

Global Luxury Suites at Reston Town Center

3.5 out of 5
11850 Freedom Drive Reston VA
Stay at this business-friendly aparthotel in Hunter Mill. Enjoy free Wi-Fi, an outdoor pool and a 24-hour health club. Popular attractions Reston Town Center ...
8.2/10 Very Good! (165 reviews)
outstanding property and great artwork!

Reviewed on 12 Mar 2026

Global Luxury Suites at Reston Town Center
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 Hunter Mill. Enjoy an outdoor pool, parking (surcharge) and a 24-hour front desk. Popular attractions Reston Town Center and ArtInsights ...
8.4/10 Very Good! (18 reviews)
Room was excellent. Exceeded our expectations

Reviewed on 7 Feb 2026

Global Luxury Suites at Town Center
Global Luxury Suites at Reston

Global Luxury Suites at Reston

4 out of 5
11410 Reston Station Blvd Reston VA
Stay at this apartment in Hunter Mill. Enjoy free Wi-Fi, an outdoor pool and parking (surcharge). Popular attractions Reston Town Center and Fair Oaks Mall are ...
7.8/10 Good! (37 reviews)
Good apartment and good location

Reviewed on 9 Mar 2026

Global Luxury Suites at Reston
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.

Popular places to visit

Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

Glenwood Park

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas or simply enjoy its restaurants.

Glenwood Park
Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon browsing the exhibits at Red Fox Fine Art during your trip to Middleburg. Visit the area's spas or simply enjoy its restaurants.

Red Fox Fine Art

Greenhill Winery & Vineyards

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this relaxing area.

Greenhill Winery & Vineyards

Middleburg Historic District

You can learn about the history of Middleburg with a visit to Middleburg Historic District.

Middleburg Historic District

Cana Vineyards and Winery

You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Dover. While in this trendy area, you can savour the top-notch restaurants.

Cana Vineyards and Winery

Chrysalis Vineyards

You can enjoy a tasting or tour at Chrysalis Vineyards during your travels to Middleburg. While in this trendy area, you can savour the top-notch restaurants.

Chrysalis Vineyards

Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

RM355
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

RM474
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Private Loudoun County Wine Tour from DC with 3 Winery Stops

Private Loudoun County Wine Tour from DC with 3 Winery Stops

RM3,907
per adult
Private Loudoun County Wine Tour from DC with 3 Winery Stops
See all activities in Middleburg