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

The Annual Holiday Sale

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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
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is £288 per night from 18 Feb to 19 Feb
£288
18 Feb - 19 Feb
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 ...
10/10 Exceptional! (55 reviews)
Loved out stay!

Reviewed on 26 Dec 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 £536 per night from 1 Mar to 2 Mar
£536
1 Mar - 2 Mar
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! (379 reviews)
Room was awesome, amazing experiences at the resort and really great customer service

Reviewed on 18 Jan 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! (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 6 Feb 2026

The Red Fox Inn & Tavern
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 ...
10/10 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.
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.

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