Middleburg vacation rentals
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Top-rated vacation rentals in Middleburg
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Middleburg
4.97 out of 5 average rating, 147 reviewsModern 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.
Dec 29 – Jan 5
Apartment in The Plains
4.97 out of 5 average rating, 439 reviewsRose 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.
Aug 15 – 22
Home in Bluemont
4.93 out of 5 average rating, 197 reviewsThe Country French Cottage at High Meadows Estate
Come visit the alluring wine country of Bluemont Virginia, and stay in a beautifully appointed country French cottage on the 50 acre circa 1896 High Meadows Estate atop the Blueridge Mountains. Just 50 minutes west of Washington DC, this stunning country retreat is just 5 minute from the vineyards of Bluemont, the Shenandoah River, the Appalachian Trail, Hiking, Canoeing, Kayaking, Farmers Markets, the the cute villages or Berryville, Harpers Ferry, Luckettes, Middleburg and many more.
Jan 26 – Feb 2
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middleburg vacation rentals
Other great vacation rentals in Middleburg
Cabin in Haymarket
4.94 out of 5 average rating, 189 reviewsLodge on the Lake
Dec 9 – 16
Home in Middleburg
4.94 out of 5 average rating, 132 reviewsThe Coach Stop at White Hall
Jul 4 – 11
Cottage in Middleburg
4.92 out of 5 average rating, 106 reviewsEnglish Cottage
May 15 – 22
Cottage in Bluemont
4.95 out of 5 average rating, 166 reviewsThe Cottage at Stonecroft
Feb 19 – 26
Tiny home in Purcellville
4.98 out of 5 average rating, 127 reviewsKing Bed-Tiny Home-Fire Pit-Historic Farm Stay
Jul 2 – 9
Home in Middleburg
4.86 out of 5 average rating, 248 reviewssuper cosy cottage with high speed internet
Jun 2 – 9
Cabin in Upperville
4.93 out of 5 average rating, 122 reviewsIsland cabin
Dec 7 – 14
Guest suite in Nokesville
4.97 out of 5 average rating, 423 reviewsHorse farm near Manassas Battlefield.
May 1 – 8
Cottage in Hamilton
4.86 out of 5 average rating, 296 reviewsRobins Nest
Jan 11 – 18
Cottage in The Plains
4.98 out of 5 average rating, 172 reviewsThe Cottage on Main -Virginia Wine & Horse Country
Feb 3 – 10
Cottage in Bluemont
4.82 out of 5 average rating, 185 reviewsWine Country Cottage
Apr 6 – 13
Home in Middleburg
4.94 out of 5 average rating, 118 reviewsLuxury Middleburg Home with 4 Bedrooms 2 Baths
Sep 20 – 27
Other great vacation rentals in Middleburg
Farm stay in Leesburg
5.0 out of 5 average rating, 110 reviewsThe Loft at Sneaky Fox Farm
Dec 12 – 19
Guest suite in Round Hill
4.94 out of 5 average rating, 112 reviewsSweet Suite on Snickersville!
May 24 – 31
Farm stay in Middleburg
4.9 out of 5 average rating, 91 reviewsSelf-contained apartment on Organic vegetable farm
Dec 12 – 19
Guesthouse in Middleburg
5.0 out of 5 average rating, 39 reviews18th Century Middleburg Cottage
Feb 18 – 25
Farm stay in Middleburg
4.94 out of 5 average rating, 34 reviewsRetreat to horse country!
Nov 5 – 12
Guesthouse in The Plains
4.97 out of 5 average rating, 37 reviewsA lovely cottage in The Plains, Virginia
Nov 5 – 12
Vacation home in The Plains
5.0 out of 5 average rating, 25 reviewsRolling Acres~1 bedroom apartment on heavenly farm
Sep 27 – Oct 4
Farm stay in Upperville
4.99 out of 5 average rating, 67 reviewsThe Ark in Upperville
May 2 – 9
Farm stay in Middleburg
4.9 out of 5 average rating, 31 reviewsGorgeous historic stone house with great internet!
Apr 29 – May 6
Cottage in Middleburg
5.0 out of 5 average rating, 17 reviewsCottage at Finnway Farm in Middleburg, VA
Mar 18 – 25
Home in Middleburg
4.95 out of 5 average rating, 41 reviewsStone Cottage, Comfort, Peace and Nature.
Jul 8 – 15
Farm stay in Bluemont
5.0 out of 5 average rating, 78 reviewsWelcome to the Hidden Hive!
Apr 18 – 23
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