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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.

Ashby's Perch -- A Very Special Retreat
SUPERHOST
Entire house · 2 guests · 1 bed · 1 bath

Ashby's Perch -- A Very Special RetreatSweeping views of Ashby's Gap just minutes away from Upperville and Middleburg, 1 hour outside of DC. Newly renovated with a vintage flair, private and secluded. Ideal weekend get-away for couples, come sample the best the Piedmont has to offer!

Waterfront Cottage at Goose Creek
SUPERHOST
Entire cottage · 3 guests · 2 beds · 1 bath

Waterfront Cottage at Goose CreekOur Cottage at Goose Creek is the perfect weekend getaway, located 2 miles from the town of Middleburg and nestled on 12 acres overlooking Goose Creek. The creek is accessible for fishing, kayaking, and exploring. Enjoy all the charm of Western Loudoun and all the amenities of nearby Middleburg.

Rose End
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Rose EndNeed 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.

Vacation rentals for every style

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Popular amenities for Middleburg vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Middleburg

SUPERHOST
  1. Entire house
  2. The Plains
Fox Cross Cottage in Virginia Horse & Wine Country
SUPERHOST
  1. Entire cottage
  2. Middleburg
Private English Cottage on Historic Country Estate
SUPERHOST
  1. Entire house
  2. Leesburg
Willow’s View
SUPERHOST
  1. Entire apartment
  2. Round Hill
The Nest of Sunny Lane Farm Fund Raiser Stay!
  1. Entire cabin
  2. Haymarket
NEW&TRENDY Getaway -The Black Aframe Haymarket, VA
SUPERHOST
  1. Entire guesthouse
  2. Round Hill
Four Winds - Private Carriage House
  1. Entire house
  2. Bluemont
Peaceful Blue Ridge Mountain Bungalow
SUPERHOST
  1. Barn
  2. Middleburg
Middleburg Carriage House
SUPERHOST
  1. Entire house
  2. Bluemont
The Country French Cottage at High Meadows Estate
SUPERHOST
  1. Entire cottage
  2. The Plains
The Cottage on Main-Virginia Wine & Horse Country
SUPERHOST
  1. Entire house
  2. Middleburg
super cosy cottage with high speed internet
SUPERHOST
  1. Farm stay
  2. Round Hill
The Log Cabin at Historic Oak Hill Farm

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