Middleburg Travel Guide

Tourist Guide

central street of the ancient town near Washington. Ancient buildings of shops, hotels and restaurants., strolling tourists.
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

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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 AU$551 per night from 10 Mar to 11 Mar
AU$551
10 Mar - 11 Mar
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! (57 reviews)
Tim is a great host. The cottage was clean, comfortable and perfectly located. Perfect place to stay for a weekend getaway to Middleburg!

Reviewed on 1 Mar 2026

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 AU$1,002 per night from 5 Apr to 6 Apr
AU$1,002
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! (384 reviews)
For over a decade, staying at Salamander Middleburg was on my bucket list. As a young professional, I always heard raving reviews but felt priced out. So when a friend and I finally secured a Presidents Day weekend stay around $600 per night, we were excited for a true luxury experience. Unfortunately, ...

Reviewed on 22 Feb 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! (425 reviews)
Lovely, clean, and spacious cottage for a special girls weekend. Check in and parking were easy and delivery of delicious, free breakfast was a special touch. Shops and restaurants just steps away.

Reviewed on 22 Feb 2026

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The Red Fox Inn & Tavern
See all 983 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 ...
10/10 Exceptional! (57 reviews)
Tim is a great host. The cottage was clean, comfortable and perfectly located. Perfect place to stay for a weekend getaway to Middleburg!

Reviewed on 1 Mar 2026

18th Century Stone Cottage minutes from historic Middleburg
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! (24 reviews)
The accomodations were clean and comfortable for our 1 night stay.

Reviewed on 15 Feb 2026

Cosy studio on an organic farm, pet friendly! Just minutes from 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! (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 29 Jan 2026

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
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 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
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

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

Activities

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

AU$127
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$170
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.