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Vacation rentals in Middleburg

Vacation rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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

  • "When Pigs Fly"  Wine Country!  Ale Trail!
    SUPERHOSTEntire loft · 2 guests · 1 bed · 1 bathroom
    "When Pigs Fly" Wine Country! Ale Trail!

    Located between Middleburg, VA and Purcellville, VA, our space is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. We offer an efficiency loft with views from every window. Although compact, we have provided all of the amenities you will need for a pleasant stay. We love our dogs and know you love yours too! We welcome your dogs while you visit. The only thing we ask is that you crate them if they are left alone.

    What guests are saying:

    “I stayed for 6 weeks at “When Pigs Fly” and loved it! Theresa and Rob were excellent hosts and went above and beyond to make sure I had everything I needed for my stay. The loft was clean, beautifully decorated, and included all the amenities needed for a long stay. I brought my dog with me, and she had plenty of space to walk around outside and around the loft. The location was beautiful, and the perfect place for a long stay or a quick trip.”

  • Middleburg Historic District Charm
    SUPERHOSTEntire house · 6 guests · 3 beds · 2 bathrooms
    Middleburg Historic District Charm

    Relax in a charming 202 year old beautifully renovated historic home. Located in the heart of Middleburg’s historic district, you’ll enjoy easy walking distance to shops and restaurants. Home is well appointed with classic antique furniture and luxury modern amenities. Experience quintessential colonial Virginia in the Middleburg village.

    What guests are saying:

    “Our Middleburg experience was absolutely charming, what a special and unique house which was within walking distance of everything from restaurants to shopping. It was so fabulous to have a swimming pool for lounging around on the hot summer day. Lindsay our host was utterly delightful starting with lining up a private chef to prepare dinner for us and be able to enjoy the lovely amenities of her beautiful and historical home. The whole experience was magical and we plan to return soon!”

  • Hunt Box  on 1700's Horse Farm/Wedding Venue
    SUPERHOSTFarm stay · 2 guests · 1 bed · 1 bathroom
    Hunt Box on 1700's Horse Farm/Wedding Venue

    The Hunt Box at Sylvanside Farm is a favorite of our couples. Cozy bedroom with bay window that overlook the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree.

    What guests are saying:

    “The Hunt Box is a lovely little cottage on Sylvanside Farm. It has a living room, full bath, bedroom with a STUNNING bay window, and a small/limited kitchen. The bed is extremely comfy. The bathroom has fluffy towels,shampoo, conditioner, body wash, lotion, hair dryer, and curling iron. The kitchen has the following: cups, bowls, plates, flatware, a few cooking utensils, french press, pourover cone, 4 burner range, tea kettle, array of cast iron pans, microwave, and tiny fridge (think the size of a wine fridge). Jeff gave us a tour of the stunning barns that are set up for events and weddings. If we weren't already married, I guarantee we would be having it here! There are 2 Clydesdales, 2 Devon cows, 3 goats, an ancient breed pig, and 2 sweet dogs. Saying hi to them every day was incredible. One day, Terri dropped off freshly laid eggs from a neighboring farm. We actually used this place as a hiking retreat since we are mid-Coronavirus and it was perfect. Lots of wide open spaces, access to the Appalachian trail, and surrounded by wine country. Whether it's for a wedding, a group stay in the bigger house, or a couple's stay, Terri and Jeff have created an idyllic spot.”

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Middleburg holiday rentals

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

Holiday rentals under £94

The average cost for a stay in Middleburg is £118/night.

Studio - Long Term Rental
Entire flat
Studio - Long Term Rental
Price:£37 / night
"When Pigs Fly"  Wine Country!  Ale Trail!
SUPERHOSTEntire loft
"When Pigs Fly" Wine Country! Ale Trail!
Price:£53 / night
Modern Brambleton Escape Minutes from IAD
Private room
Modern Brambleton Escape Minutes from IAD
Price:£27 / night
Serenity on the Shenandoah River
Entire guest house
Serenity on the Shenandoah River
Price:£65 / night
Four Winds  -  Private Carriage House
SUPERHOSTEntire guest house
Four Winds - Private Carriage House
Price:£85 / night
Private, Cozy and Spacious Basement Suite
SUPERHOSTEntire house
Private, Cozy and Spacious Basement Suite
Price:£39 / night
Great place to relax
Private room
Great place to relax
Price:£28 / night
Brews & Views ~ Cottage at Dirt Farm Brewing
SUPERHOSTEntire cottage
Brews & Views ~ Cottage at Dirt Farm Brewing
Price:£81 / night
Rose End
Entire flat
Rose End
Price:£61 / night
Comfy Blue Ridge Mountains Log Cabin (Ravenswood)
SUPERHOSTPrivate room
Comfy Blue Ridge Mountains Log Cabin (Ravenswood)
Price:£41 / night
Inexpensive long term Lodgings
Private room
Inexpensive long term Lodgings
Price:£26 / night
Quiet comfort Private Room  (V2)
Private room
Quiet comfort Private Room (V2)
Price:£28 / night
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