Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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

Guest favourite

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

$631 CAD per night
Guest favourite

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

$129 CAD per night
Guest favourite

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

$237 CAD 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 favourite

Cabin in Haymarket

4.94 out of 5 average rating, 189 reviews

Lodge on the Lake

Sep. 17 – 24

$511 CAD per night
Guest favourite

Cottage in Middleburg

4.92 out of 5 average rating, 106 reviews

English Cottage

May 15 – 22

$271 CAD per night
Superhost

Home in Middleburg

4.94 out of 5 average rating, 132 reviews

The Coach Stop at White Hall

Jul. 5 – 12

$642 CAD per night
Guest favourite

Cottage in Bluemont

4.95 out of 5 average rating, 166 reviews

The Cottage at Stonecroft

Feb. 19 – 26

$223 CAD per night
Guest favourite

Home in Middleburg

4.86 out of 5 average rating, 248 reviews

super cosy cottage with high speed internet

Jun. 9 – 16

$461 CAD per night
Guest favourite

Cabin in Upperville

4.93 out of 5 average rating, 122 reviews

Island cabin

Dec. 7 – 14

$400 CAD per night
Guest favourite

Guest suite in Nokesville

4.97 out of 5 average rating, 423 reviews

Horse farm near Manassas Battlefield.

May 1 – 8

$122 CAD per night
Guest favourite

Cottage in The Plains

4.98 out of 5 average rating, 172 reviews

The Cottage on Main -Virginia Wine & Horse Country

Feb. 3 – 10

$307 CAD per night
Guest favourite

Farm stay in Middleburg

4.9 out of 5 average rating, 91 reviews

Self-contained apartment on Organic vegetable farm

Dec. 12 – 19

$244 CAD per night
Guest favourite

Guesthouse in Middleburg

5.0 out of 5 average rating, 39 reviews

18th Century Middleburg Cottage

Feb. 18 – 25

$377 CAD per night
Guest favourite

Farm stay in Middleburg

4.94 out of 5 average rating, 34 reviews

Retreat to horse country!

Nov. 5 – 12

$409 CAD 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

$221 CAD per night

Destinations to explore

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