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.

Guest favorite

Home in Middleburg

4.97 out of 5 average rating, 147 reviews

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.

Dec 29 – Jan 5

$339 per night
Guest favorite

Apartment in The Plains

4.97 out of 5 average rating, 439 reviews

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.

Aug 15 – 22

$77 per night
Guest favorite

Home in Bluemont

4.93 out of 5 average rating, 197 reviews

The 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

$124 per night

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

Cabin in Haymarket

4.94 out of 5 average rating, 189 reviews

Lodge on the Lake

Dec 9 – 16

$266 per night
Superhost

Home in Middleburg

4.94 out of 5 average rating, 132 reviews

The Coach Stop at White Hall

Jul 4 – 11

$328 per night
Guest favorite

Cottage in Middleburg

4.92 out of 5 average rating, 106 reviews

English Cottage

May 15 – 22

$149 per night
Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 166 reviews

The Cottage at Stonecroft

Feb 19 – 26

$121 per night
Guest favorite

Tiny home in Purcellville

4.98 out of 5 average rating, 127 reviews

King Bed-Tiny Home-Fire Pit-Historic Farm Stay

Jul 2 – 9

$187 per night
Guest favorite

Home in Middleburg

4.86 out of 5 average rating, 248 reviews

super cosy cottage with high speed internet

Jun 2 – 9

$250 per night
Guest favorite

Cabin in Upperville

4.93 out of 5 average rating, 122 reviews

Island cabin

Dec 7 – 14

$226 per night
Guest favorite

Guest suite in Nokesville

4.97 out of 5 average rating, 423 reviews

Horse farm near Manassas Battlefield.

May 1 – 8

$67 per night
Superhost

Cottage in Hamilton

4.86 out of 5 average rating, 296 reviews

Robins Nest

Jan 11 – 18

$125 per night
Guest favorite

Cottage in The Plains

4.98 out of 5 average rating, 172 reviews

The Cottage on Main -Virginia Wine & Horse Country

Feb 3 – 10

$170 per night
Superhost

Cottage in Bluemont

4.82 out of 5 average rating, 185 reviews

Wine Country Cottage

Apr 6 – 13

$78 per night
Superhost

Home in Middleburg

4.94 out of 5 average rating, 118 reviews

Luxury Middleburg Home with 4 Bedrooms 2 Baths

Sep 20 – 27

$398 per night

Other great vacation rentals in Middleburg

Guest favorite

Farm stay in Leesburg

5.0 out of 5 average rating, 110 reviews

The Loft at Sneaky Fox Farm

Dec 12 – 19

$229 per night
Guest favorite

Guest suite in Round Hill

4.94 out of 5 average rating, 112 reviews

Sweet Suite on Snickersville!

May 24 – 31

$98 per night
Guest favorite

Farm stay in Middleburg

4.9 out of 5 average rating, 91 reviews

Self-contained apartment on Organic vegetable farm

Dec 12 – 19

$132 per night
Guest favorite

Guesthouse in Middleburg

5.0 out of 5 average rating, 39 reviews

18th Century Middleburg Cottage

Feb 18 – 25

$219 per night
Guest favorite

Farm stay in Middleburg

4.94 out of 5 average rating, 34 reviews

Retreat to horse country!

Nov 5 – 12

$210 per night
Guest favorite

Guesthouse in The Plains

4.97 out of 5 average rating, 37 reviews

A lovely cottage in The Plains, Virginia

Nov 5 – 12

$149 per night
Superhost

Vacation home in The Plains

5.0 out of 5 average rating, 25 reviews

Rolling Acres~1 bedroom apartment on heavenly farm

Sep 27 – Oct 4

$122 per night
Guest favorite

Farm stay in Upperville

4.99 out of 5 average rating, 67 reviews

The Ark in Upperville

May 2 – 9

$131 per night
Guest favorite

Farm stay in Middleburg

4.9 out of 5 average rating, 31 reviews

Gorgeous historic stone house with great internet!

Apr 29 – May 6

$493 per night
Guest favorite

Cottage in Middleburg

5.0 out of 5 average rating, 17 reviews

Cottage at Finnway Farm in Middleburg, VA

Mar 18 – 25

$500 per night
Guest favorite

Home in Middleburg

4.95 out of 5 average rating, 41 reviews

Stone Cottage, Comfort, Peace and Nature.

Jul 8 – 15

$261 per night
Guest favorite

Farm stay in Bluemont

5.0 out of 5 average rating, 78 reviews

Welcome to the Hidden Hive!

Apr 18 – 23

$144 per night

Destinations to explore

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