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Middleburg vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Middleburg

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

Guest favorite
Cottage in The Plains
The Cottage on Main -Virginia Wine & Horse Country
The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!
Mar 20 – 27
$157 per night
4.98 out of 5 average rating, 172 reviews
Guest favorite
Guest suite in Nokesville
Horse farm near Manassas Battlefield.
Comfortable accommodations for horses and the people traveling with them. Private suite, private entrance (bedroom, bath, kitchenette) + 2 RV hookups water/electric. 6 stalls - nice paddock turnout. Lighted arena. Close to: Manassas Battlefield (25 mile trail); Skymeadow State Park (nice trails); several hunt clubs; VRE connections - to METRO; 3 miles to Manassas airport. Not accepting pets for the time being. Several wineries and breweries within 12 miles - ONLY 6 miles to Jiffy Lube Live.
Apr 28 – May 5
$67 per night
4.97 out of 5 average rating, 422 reviews
Guest favorite
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.
Aug 30 – Sep 6
$357 per night
4.97 out of 5 average rating, 147 reviews

Popular amenities for Middleburg vacation 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 vacation rentals in Middleburg

Guest favorite
Tiny home in Purcellville
King Bed-Tiny Home-Fire Pit-Historic Farm Stay
Jul 6 – 13
$174 per night
4.98 out of 5 average rating, 125 reviews
Guest favorite
Home in Middleburg
Luxury Middleburg Home with 4 Bedrooms 2 Baths
Nov 6 – 13
$440 per night
4.94 out of 5 average rating, 118 reviews
Guest favorite
Cabin in Haymarket
Lodge on the Lake
Oct 8 – 15
$270 per night
4.94 out of 5 average rating, 188 reviews
Guest favorite
Farm stay in Leesburg
Farm Retreat in the Heart of Loudoun Wine Country!
Aug 10 – 17
$139 per night
4.98 out of 5 average rating, 188 reviews
Guest favorite
Home in Bluemont
The Country French Cottage at High Meadows Estate
Sep 30 – Oct 7
$124 per night
4.93 out of 5 average rating, 195 reviews
Guest favorite
Cottage in Middleburg
English Cottage
Jun 26 – Jul 3
$149 per night
4.92 out of 5 average rating, 106 reviews
Guest favorite
Home in Middleburg
The Coach Stop at White Hall
May 23 – 30
$328 per night
4.94 out of 5 average rating, 132 reviews
Guest favorite
Tiny home in Purcellville
Remote Tiny House in Purcellville
Jun 23 – 30
$136 per night
4.96 out of 5 average rating, 309 reviews
Guest favorite
Farm stay in Round Hill
Come and get your goat on!
Jul 14 – 21
$109 per night
4.94 out of 5 average rating, 339 reviews
Superhost
Cottage in Upperville
Cottage on Pantherskin Creek - Upperville
Apr 5 – 12
$198 per night
4.87 out of 5 average rating, 109 reviews
Guest favorite
Cottage in Aldie
Status House at the Little River Inn
Aug 5 – 12
$212 per night
4.97 out of 5 average rating, 100 reviews
Guest favorite
Cabin in Upperville
Island cabin
Apr 6 – 13
$213 per night
4.93 out of 5 average rating, 121 reviews

Other great vacation rentals in Middleburg

Guest favorite
Home in Paris
Ashby's Perch -- A Very Special Retreat
Jul 3 – 10
$300 per night
4.97 out of 5 average rating, 303 reviews
Guest favorite
Farm stay in Middleburg
Self-contained apartment on Organic vegetable farm
Nov 13 – 20
$132 per night
4.9 out of 5 average rating, 91 reviews
Guest favorite
Guesthouse in Middleburg
18th Century Middleburg Cottage
Nov 10 – 17
$219 per night
5.0 out of 5 average rating, 38 reviews
Guest favorite
Guesthouse in The Plains
A lovely cottage in The Plains, Virginia
Dec 29 – Jan 5
$148 per night
4.97 out of 5 average rating, 37 reviews
Guest favorite
Guesthouse in Middleburg
Romantic Carriage House - 1 Bedroom Loft Apt
Apr 9 – 16
$143 per night
4.96 out of 5 average rating, 69 reviews
Guest favorite
Farm stay in Middleburg
Retreat to horse country!
Dec 19 – 26
$237 per night
4.94 out of 5 average rating, 34 reviews
Guest favorite
Home in Middleburg
Countryside cottage quiet setting in Middleburg
May 23 – 30
$267 per night
5.0 out of 5 average rating, 50 reviews
Guest favorite
Home in Middleburg
Stone Cottage, Comfort, Peace and Nature.
May 30 – Jun 6
$309 per night
4.95 out of 5 average rating, 41 reviews
Guest favorite
Farm stay in Middleburg
Gorgeous historic stone house with great internet!
Jun 30 – Jul 7
$650 per night
4.9 out of 5 average rating, 31 reviews
Guest favorite
Cottage in Middleburg
Cottage at Finnway Farm in Middleburg, VA
Mar 24 – 31
$500 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Farm stay in Upperville
The Ark in Upperville
May 22 – 29
$131 per night
4.99 out of 5 average rating, 67 reviews
Superhost
Vacation home in The Plains
Rolling Acres~1 bedroom apartment on heavenly farm
Sep 21 – 28
$121 per night
5.0 out of 5 average rating, 25 reviews

Destinations to explore

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