Middleburg, VA

Travel Guide

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
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

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

Downtown
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is ￥42,141 per night from Feb 18 to Feb 19
￥42,141
￥60,346 total
Feb 18 - Feb 19
includes taxes & fees
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! (55 reviews)
Loved out stay!

Reviewed on Dec 26, 2025

18th Century Stone Cottage minutes from historic Middleburg
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
The price is ￥91,178 per night from Feb 24 to Feb 25
￥91,178
￥111,902 total
Feb 24 - Feb 25
includes taxes & 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 ...
9.2/10 Wonderful! (379 reviews)
Room was awesome, amazing experiences at the resort and really great customer service

Reviewed on Jan 18, 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 WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Red ...
9.6/10 Exceptional! (424 reviews)
Cottage not suitable for winter rentals. Too cold in room to be comfortable despite extra blankets, and space heater. Staff very friendly and helpful. We were expecting a lot more pampering for the money spent ( like being offered a warmer room!)

Reviewed on Feb 6, 2026

Get rates
The Red Fox Inn & Tavern
See all 993 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! (55 reviews)
Loved out stay!

Reviewed on Dec 26, 2025

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! (1 review)
Everything was great and our dogs had a blast.

Reviewed on Oct 12, 2025

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Middleburg VA
Stay at this apartment in Middleburg. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Cana Vineyards and Winery and Greenhill Winery ...
9.8/10 Exceptional! (23 reviews)
Lovely clean room.

Reviewed on Dec 26, 2025

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
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

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 studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

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

Glenwood Park

5/5(1 review)

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

Greenhill Winery & Vineyards

3.5/5(3 reviews)

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 trip to Middleburg Historic District.

Middleburg Historic District

Chrysalis Vineyards

4/5(2 reviews)

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

Chrysalis Vineyards

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 savor the top-notch restaurants.

Cana Vineyards and Winery

Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

￥13,930
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

￥17,024
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Virginia Wineries Tour

Virginia Wineries Tour

￥38,695
per traveler
Virginia Wineries Tour
See all activities in Middleburg

Reviews of Middleburg

4.7
Top Destination
5 - Excellent
22
5 - Excellent 73%
4 - Good
7
4 - Good 23%
3 - Okay
1
3 - Okay 3%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Went there for wineries. Had a wonderful experience.

4/5 - Good

Verified traveler

It's a gorgeous countryside getaway!

5/5 - Excellent

MC

Quant town near a major sites.

3/5 - Okay

Verified traveler

Stores are a little dated

5/5 - Excellent

Verified traveler

Cute town. With good food and unique places to shop! Loved our stay on this town!

5/5 - Excellent

Verified traveler

Centrally located to wineries and breweries in the general surrounding areas.

Cities near Middleburg

Historic Oatlands Plantation in Leesburg, VA

Leesburg

Purcellville Town Hall, 221 South Nursery Avenue, Purcellville, Virginia

Purcellville

Vineyard views at Bluemont Vineyard in northern Virginia.

Bluemont

There's nothing better than taking drives in the fall. I love all autumnal things and spotting beautiful driveways with rich colors such as this is worth pulling over and taking a few pictures. I'm jealous of whoever lives here.

Aldie

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