5/5 - Excellent
Verified traveler
Went there for wineries. Had a wonderful experience.
Middleburg, VA
Travel Guide
Visit Middleburg
Where to stay in Middleburg
Downtown
While visiting Downtown, you might make a stop by sights like Middleburg Historic District and Red Fox Fine Art.
18th Century Stone Cottage minutes from historic Middleburg
Middleburg VA
The price is AED 1,010 per night from Mar 1 to Mar 2
AED 1,010
AED 1,446 total
1 Mar - 2 Mar
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! (56 reviews)
Had an excellent time staying here, it was a blend if rustic and modern. Very cozy, and had everything you'd need for a truly relaxing stay. Tim made sure everything was on point for our time at the cottage.
Reviewed on 22 February 2026
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
The price is AED 2,185 per night from Mar 5 to Mar 6
AED 2,185
AED 2,682 total
5 Mar - 6 Mar
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! (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 February 2026
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
The price is AED 2,711 per night from Mar 28 to Mar 29
AED 2,711
AED 3,091 total
28 Mar - 29 Mar
includes taxes & fees
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! (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 February 2026
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
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! (56 reviews)
Had an excellent time staying here, it was a blend if rustic and modern. Very cozy, and had everything you'd need for a truly relaxing stay. Tim made sure everything was on point for our time at the cottage.
Reviewed on 22 February 2026
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! (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 January 2026
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 26 December 2025
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 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.
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.
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.
Middleburg Historic District
You can learn about the history of Middleburg with a trip to 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 savor the top-notch restaurants.
Chrysalis Vineyards
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.
Reviews of Middleburg
4.7
Top Destination
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.
