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Middleburg holiday lettings

We found 417 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 11 homes and other holiday rentals in Middleburg that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting scenic Middleburg

Enjoy the wineries and other features of Middleburg. This scenic and relaxing city is well known for its spas, horse riding and restaurants. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Middleburg

Are you hoping to discover things to do during your stay? Venture out of your holiday home and check out everything that makes Middleburg a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Greenhill Winery & Vineyards (1.6 mi / 2.6 km)
  • Chrysalis Vineyards (3.4 mi / 5.4 km)
  • Cana Vineyards and Winery (3.7 mi / 5.9 km)
  • Quattro Goomba's Winery (6.5 mi / 10.4 km)
  • Stone Tower Winery (8.5 mi / 13.7 km)
  • Bluemont Vineyard (10.4 mi / 16.7 km)

Exploring the natural features in Middleburg

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Middleburg is a great place to get outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Sky Meadows State Park (12 mi / 19.2 km)
  • Manassas National Battlefield Park (15 mi / 24.2 km)
  • Morven Park (15.1 mi / 24.3 km)
  • Shenandoah Lake Beach (17.2 mi / 27.7 km)
  • Frying Pan Farm Park (17.6 mi / 28.3 km)
  • Shenandoah River (24.4 mi / 39.2 km)

Transport options to and around Middleburg

Fly into Washington Dulles International Airport (IAD), the closest airport, located 15.5 mi (24.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Manassas, VA (MNZ-Manassas Regional), which is 20.6 mi (33.2 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Middleburg?

Houses are the most popular style of holiday rental in Middleburg, according to our data. Even if you've got something a little different in mind, Vrbo has holiday homes in loads of sizes and shapes. Browse our options to find your perfect Middleburg pad.

How much does it cost to rent a holiday rental in Middleburg?

The average price for a holiday home in Middleburg is determined by several factors, like property type, length of stay and season. Whether you're dreaming about a sprawling villa with room to move around or a cosy cottage ideal for just you and the kids, just enter your dates of travel to see stays that offer great value.

How much does it cost to rent a beach house in Middleburg?

The average price for a holiday home near the beach in Middleburg depends on when you're visiting the area and the style and size of property you're looking for. You can easily find prices on Vrbo by entering your destination and travel dates. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.

Are there pet-friendly holiday rentals in Middleburg?

You're in luck. There are. You'll find three holiday rentals that allow pets in Middleburg on Vrbo. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to book a place where your puppy dog can be near his favourite humans.

What are popular rental amenities in Middleburg?

A barbecue grill, a firepit and a garden top the list of most popular rental amenities in Middleburg. Whether you plan to go as a party of one, with your spouse or a group of best friends, Vrbo will help you find a holiday rental that matches your style with all the conveniences you're looking for.

Are there large group holiday rentals in Middleburg?

With two Middleburg holiday properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a special celebration, Vrbo will help you book the perfect space to fit the occasion.

Are there holiday rentals in Middleburg that welcome kids?

Bring the entire family together for fun-filled adventures in Middleburg at one of our three family-friendly holiday properties. Lots of these stays come with amenities that are suitable for getaways with children, including full kitchens, bunk beds and entertainment units. Just check the "Properties good for families" filter box and choose your favourite option.

What are the top attractions for families in Middleburg?

There are lots of fabulous things to do and see with the family in Middleburg, such as:

  • National Sporting Library & Museum
  • Red Fox Fine Art
  • The Sporting Gallery

How can I find holiday rentals with air conditioning in Middleburg?

Select your travel dates and then use our filters to view holiday rentals with ac in Middleburg on Vrbo. With three air-conditioned properties to choose from here, you can look forward to a comfy and cool stay.

How old do you have to be to rent a holiday rental in Middleburg?

The minimum age is normally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your chosen Middleburg stay before making a booking.

How long can I rent a holiday rental in Middleburg for?

The amount of time you can stay in a Middleburg holiday home for depends on the property. Simply enter your preferred travel dates to see options offering longer term stays. They come with the things you need to make your extended getaway more comfortable and enjoyable, like air conditioning and kitchens. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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