Middleburg Travel Guide

Tourist 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

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 AU$1,081 per night from 25 Jan to 26 Jan
AU$1,081
25 Jan - 26 Jan
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! (376 reviews)
Great

Reviewed on 1 Jan 2026

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

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is AU$574 per night from 28 Jan to 29 Jan
AU$574
28 Jan - 29 Jan
includes taxes & fees
Stay at this cottage in Middleburg. Enjoy free Wi-Fi, a garden and patios. Popular attractions The Boxwood Winery and Middleburg Community Center are located ...
9.8/10 Exceptional! (55 reviews)
Loved out stay!

Reviewed on 26 Dec 2025

18th Century Stone Cottage minutes from historic Middleburg
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
The price is AU$525 per night from 25 Jan to 26 Jan
AU$525
25 Jan - 26 Jan
includes taxes & fees
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! (420 reviews)
By far one of the best inns I've stayed at. The sraff and service was excellent. Dining was outstanding. Every detail impeccably designed. Will be back soon!

Reviewed on 17 Jan 2026

The Red Fox Inn & Tavern
See all 989 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 Wi-Fi, a garden and patios. Popular attractions The Boxwood Winery and Middleburg Community Center are located ...
9.8/10 Exceptional! (55 reviews)
Loved out stay!

Reviewed on 26 Dec 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 holiday 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 12 Oct 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 Wi-Fi, a garden and an in-room coffee maker. Popular attractions Cana Vineyards and Winery and Greenhill Winery ...
9.8/10 Exceptional! (23 reviews)
Lovely clean room.

Reviewed on 26 Dec 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

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

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

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

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

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

Activities

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

AU$134
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

AU$166
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
See all activities in Middleburg

Reviews of Middleburg

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5/5 - Excellent

Verified traveller

Middleburg is a lovely town. So charming and picturesque, with some great eateries and shops, a lot of history, and set in gorgeous countryside. Wish we could stay longer.