Holiday rentals in Middleburg

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Popular amenities for Middleburg holiday rentals

Stay near Middleburg's top sights

Salamander Resort & Spa47 locals recommend
The Red Fox Inn & Tavern44 locals recommend
The Boxwood Winery25 locals recommend
National Sporting Library & Museum22 locals recommend
Middleburg Common Grounds21 locals recommend
Red Horse Tavern LLC20 locals recommend

Other great holiday rentals in Middleburg

Guest favourite
Cabin in Augusta ( Capon Bridge)
4.97 out of 5 average rating, 149 reviews

Nirvana, Mountain View

RafaelRating, 5 stars1 month ago
We had an amazing stay, it's a very well equipped cabin, in an amazing, beautiful and very quiet place, exactly the kind of retreat we were looking for. Great mountais view. The nearby town is also very quiet and receptive, where it's easy to buy food and supplies. Su and her husband are amazing people and always willing to help. I can't wait to go back.
Guest favourite
Home in Cross Junction
4.87 out of 5 average rating, 119 reviews

The Little Red Schoolhouse

Rebecca,RobinsonRating, 5 stars4 weeks ago
I will say excellent things about this place. I will say excellent things about this place. Welcome to the schoolhouse, where the decor and environment remind you of days of yore. With a gorgeous views especially out the back and kitchen side, we enjoyed watching the sunset from the hot tub. We enjoyed an outing of a hike in the PawPaw tunnel, and had some food at Cheryl's Snack Shack. We were seeking a private place with easy access but felt remote, within a couple hours from home. We achieved that goal, and we enjoyed ourselves. Kitchen was fully stocked. Plenty of towels for the hot tub.
Guest favourite
Home in Annandale
4.94 out of 5 average rating, 16 reviews

Family Ready Dogs OK Ping Pong Backyard EV Charger

BenjaminRating, 5 stars2 weeks ago
We had an amazing stay at this charming and cozy home—it truly felt like a dream! From the moment we arrived, we felt welcomed and at ease. The space was incredibly inviting, with thoughtful touches throughout that made it feel like a true home away from home. It was the perfect spot for our work team—spacious enough to accommodate everyone comfortably, and the common areas were ideal for team meetings and collaboration. After a long day at work, it was such a relief to come back to this peaceful and comfortable retreat. The kitchen was well-equipped, and the cozy furnishings made it easy to unwind and relax. The hosts clearly put a lot of care into making sure guests have a fantastic experience. We couldn’t have asked for a better place to stay, and we’ll definitely be back in the future! Highly recommend!
Superhost
Home in Harpers Ferry
4.83 out of 5 average rating, 246 reviews

Larger Families, Hot tub, Campfire Ring, Rural

PatriceRating, 5 stars1 month ago
Our family really enjoyed our stay! Steps away from snow tubing and the restaurant. Spacious, clean home with all the amenities of home! Definitely coming back!
Guest favourite
Home in Luray
4.89 out of 5 average rating, 79 reviews

Log house in blue

MeghanRating, 5 stars3 weeks ago
Loved Nancy’s blue lodge. Really appreciated the flexible check in, having the whole lodge with the dogs made it a great getaway weekend. The appliances seemed brand new and the bed was super comfy with plenty of clean towels and linens. Thank you Nancy for having us.
Superhost
Flat in Luray
4.85 out of 5 average rating, 53 reviews

Downtown Luray Getaway ~ Walk to Everything

Bujji SettyRating, 5 stars1 month ago
Had a great stay, was exactly what we were looking for to enjoy time in the national park.
Superhost
Home in Germantown
4.79 out of 5 average rating, 53 reviews

Sophia’s victorian

ToddRating, 5 stars3 months ago
This is the second year that we’ve stayed and I have nothing but good things to say about the property and the hosts. Always great experience, house is always spotless, the hosts are always responsive and the location for us was perfect. Thank you!
Guest favourite
Cottage in Front Royal
5 out of 5 average rating, 29 reviews

St. Anne's Cottage with peaceful farm views

PatriciaRating, 5 stars8 months ago
This was a beautiful home with lots of room for our group to spread out. We all had our own private space as well as several common areas to hang out together. The house was clean, spacious, and had great views. Thanks for the great stay!

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Loudoun County
  5. Middleburg