Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.
14–21 AugIndividual Host,
£377 per night
4.98 out of 5 average rating, 146 reviews
Guest favourite
Flat in The Plains
Rose End
Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.
8–15 Aug
£75 per night
4.97 out of 5 average rating, 431 reviews
Guest favourite
Loft in Purcellville
"When Pigs Fly" Airbnb Most Hospitable Host in VA
Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.
1–8 Sept
£107 per night
4.99 out of 5 average rating, 281 reviews

Popular amenities for Middleburg holiday rentals

Stay near Middleburg's top sights

Salamander Resort & Spa47 locals recommend
The Red Fox Inn & Tavern44 locals recommend
Red Horse Tavern LLC20 locals recommend
Middleburg Common Grounds21 locals recommend
Market Salamander11 locals recommend
Safeway16 locals recommend

Other great holiday rentals in Middleburg

Guest favourite
Barn in Middleburg
Middleburg Carriage House
6–13 Nov
£265 per night
4.93 out of 5 average rating, 171 reviews
Guest favourite
Guest house in Round Hill
Private Carriage House
10–17 Apr
£126 per night
4.98 out of 5 average rating, 366 reviews
Guest favourite
Cabin in Haymarket
Lodge on the Lake
25 Oct – 1 Nov
£292 per night
4.94 out of 5 average rating, 188 reviews
Guest favourite
Guest suite in The Plains
Luxury hunt country getaway!
23–30 MayIndividual Host,
£173 per night
5.0 out of 5 average rating, 113 reviews
Superhost
Cottage in Upperville
Cottage on Pantherskin Creek - Upperville
16–23 JunProfessional Host,
£202 per night
4.87 out of 5 average rating, 106 reviews
Guest favourite
Tiny home in Purcellville
King Bed-Tiny Home-Fire Pit-Historic Farm Stay
6–13 Jun
£186 per night
4.98 out of 5 average rating, 124 reviews
Guest favourite
Farm stay in Purcellville
Cozy Cuddle up on 1700’s Clydesdale Farm
30 Mar – 6 AprIndividual Host,
£192 per night
4.99 out of 5 average rating, 303 reviews
Superhost
Home in Middleburg
Luxury Middleburg Home with 4 Bedrooms 2 Baths
13–20 FebProfessional Host,
£428 per night
4.94 out of 5 average rating, 118 reviews
Guest favourite
Cottage in Leesburg
The Cottage at Stone Tower Winery
21–28 DecProfessional Host,
£288 per night
4.92 out of 5 average rating, 182 reviews
Guest favourite
Place to stay in The Plains
The Whistle Stop
6–13 MayIndividual Host,
£134 per night
4.94 out of 5 average rating, 159 reviews
Guest favourite
Cabin in Upperville
Island cabin
19–26 Feb
£229 per night
4.93 out of 5 average rating, 121 reviews
Guest favourite
Cottage in The Plains
The Cottage on Main-Virginia Wine & Horse Country
17–24 JulIndividual Host,
£198 per night
4.98 out of 5 average rating, 171 reviews

Destinations to explore

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  4. Loudoun County
  5. Middleburg