Discover a selection of 88 vacation rentals in Middleburg, VA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $97 per night, and houses and cottages are popular options for a stay in Middleburg. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Middleburg
Destination guide

Why people love visiting beautiful Middleburg

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

Things to do

A rich heritage of outdoor pursuits

You'll not be disappointed with the things to do in town when you stay in a Middleburg vacation rental. The National Sporting Library & Museum was founded more than 50 years ago and houses information archives and artifacts which highlight the region's heritage. If you're interested in historic buildings, be sure to visit the Aldie Mill, a 19th century fully operational mill which offers live grinding demonstrations to visitors. Alternatively, visit one of the many wineries from Greenhill to 50 West Vineyards to learn about wine production and sample some excellent vintages.


Saddle up in Middleburg

Middleburg's relatively moderate climate and proximity to state parks make it an ideal base for many outdoor activities throughout the year. If you're a mountain biker, you can ride down the challenging routes that wind through the nearby forests, or lace up your hiking boots to walk along the scenic paths that include a section of the famous Appalachian Trail. This is fox hunting territory, so there's never a shortage of horseback riders to take you on thrilling trips through the nearby valleys. You'll always be able to find an adventure that's right for you.


All 4 seasons await in Middleburg

Virginia summers are hot, but the breeze can cool the town down and make it ideal for exploration. It's popular in July and August, so be sure to book your Middleburg vacation rental early to avoid disappointment. Both spring and fall can be wonderful with bright, sunny days and far fewer visitors to contend with around the town or on the hiking trails. Winter usually brings in flurries of snow and the temperature drops to well below freezing, but you can hole up in one of the cozy restaurants or cafes and sample the delicious cuisine.

Natural features

Explore Sky Meadows State Park

Just 20 miles or so west of your Middleburg vacation rental is the Sky Meadows State Park, a land of rolling green meadows and scenic woodland on the side of the Blue Ridge Mountains. It's popular with hikers and anglers, and provides an important habitat for bird species. Year round, birders descend onto the park to see the different species of woodpeckers, particularly the colony of red-headed examples which nest in the oak groves. If you go at the right time, you may be able to join one of the regular astronomy nights led by experts from the Smithsonian Institution.

How to get there

Transportation options to and around Middleburg

Fly into Washington Dulles Intl. Airport (IAD), the closest airport, located 15.5 mi (24.9 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Ronald Reagan Washington National Airport (DCA), which is 38.2 mi (61.5 km) away.

What are the top vacation rentals in or near Middleburg?

Whether you're seeking a cozy escape for you and your boo or someplace spacious to fit family and friends, you'll find some top vacation rentals in and around Middleburg. Here are a couple we think you'll like:

  • Make the most of handy amenities like mountain views and air conditioning at "Three Bedroom Short Term Rental House On Historic Linden Hall Farm". Located around 20 miles from Middleburg, this vacation rental has 3 bedrooms and is a hit with guests.
  • Alternatively, unpack your suitcase at "Cedar Lane - Private Cottage, Sophisticated Country Charm". Around 2 miles from the heart of Middleburg, it has 2 bedrooms and comes with spa and beauty services and a hair dryer.

For even more great options, use the search bar at the top of the page to find the perfect Middleburg vacation rental for you.

Can I find log cabins to rent in or near Middleburg?

Whether you're on the lookout for a log cabin for a break with your buddies or a family adventure, Vrbo has the ideal property for you. Consider one of these terrific vacation rentals in or near Middleburg and enjoy being surrounded by nature for a while:

  • "Beautiful Blueridge Mountain Cedar Log Cabin With A Breathtaking View" has all the comforts you need for a relaxed getaway, including a smart TV and a stovetop. Once you've settled in, venture out and take in the lovely scenery.
  • You won't have to give up any home comforts if you stay at "Entire Log Cabin Vacation Rental 4 Bedroom Contact Us For Availability". This escape features a kitchen, a stovetop and more.

What are the top-rated vacation rentals for weekend getaways in or near Middleburg?

Get far away from the busyness of everyday life at one of our weekend getaways in or near Middleburg. Whether you'd like to catch up with friends or spend treasured time with the fam, we'll have something to suit your needs. These top-rated options are hard to beat:

  • "Breathtaking Views With An Indoor Private Pool" is around 10 miles northwest of Middleburg and the perfect place to relax and unwind. You'll appreciate the convenient amenities here, including pet-friendly services and an oven.
  • "Middleburg Carriage House" is another fantastic option. It's located 2 miles to the southeast of Middleburg and features a microwave oven, a hair dryer and more.

Can I find studio apartments for rent in and around Middleburg?

Studio apartments may be on the smaller side, but they sure do pack a punch when it comes to location and convenience. Put your bags down at one of these quality studio apartments in and around Middleburg:

  • Enjoy some time out on your own or take a few buddies along to "5 Min To Middleburg - Private Guest Suite". You'll have plenty of amenities at your disposal, including off-street parking options and high-speed internet services.
  • "Hunt Box On 1700's Horse Farm/wedding Venue" is another top stay, providing all you could want for the ideal Middleburg vacation. Convenient amenities here include free toiletries and WiFi.

Can I find short term rentals in or near Middleburg?

Whether you're looking for a compact apartment or a large vacation home, you'll find the ideal place on Vrbo. Sneak in some downtime at one of these getaways in or near Middleburg:

  • For a wonderful night or two away, settle in at "Elegant Middleburg Manor With 3 Bedrooms 2 Baths". It's nice and close to the center of Middleburg, along with lots of things to put on your itinerary.
  • Another fantastic option is "Littlefield Cottage". Gather a few friends and enjoy a relaxing stay near the heart of Middleburg.

What are the best romantic weekend getaways in or near Middleburg?

Whether spent in a cabin, a cottage or a condo, a romantic weekend getaway is a wonderful way to spice up your love life. Whisk your partner off for a few days at one of these sought-after escapes in or near Middleburg:

  • Sneak away on Friday for a couple of passionate nights at "Three Bedroom Short Term Rental House On Historic Linden Hall Farm". Approximately 20 miles from Middleburg, this property comes with lots of nice touches, including winery tours and outdoor furniture.
  • Another place where you can enjoy a few glorious days together is "Cedar Lane - Private Cottage, Sophisticated Country Charm". Located around 2 miles from Middleburg, winery tours and a fireplace add to the atmosphere here.

What are the best large group vacation rentals in or near Middleburg?

Browse these large group vacation rentals in or near Middleburg where you won't have to leave anyone off your invite list:

  • Offering privacy, space and comfort, you'll get your guests' tick of approval at "Breathtaking Views With An Indoor Private Pool". Up to 14 people can be accommodated at this retreat which has 6 bedrooms, mountain views and a sauna. This group getaway is around 10 miles to the northwest of Middleburg.
  • Invite up to 12 of your favorite people to "Maple Hill Farm Within Minutes Of Vineyards" and fill its spaces with laughter and love. This popular option has 4 bedrooms and is around 4 miles to the north of Middleburg. It's packed with features to keep your group happy and comfortable, such as a nearby river and a fireplace.

What are the best houses for rent with a pool in or near Middleburg?

Nothing screams fun like a pool. Grab your inflatable doughnut and browse these houses in or near Middleburg that come with this added perk:

  • Treat your loved ones to an unforgettable stay at "Three Bedroom Short Term Rental House On Historic Linden Hall Farm". There's a lot to love about this escape apart from its pool, such as coffee and tea making facilities and cable/satellite TV services.
  • "Middleburg Carriage House" is the kind of place you go to get away from it all and appreciate your surroundings, starting with its awesome pool. Pet-friendly facilities and a fridge are also on hand to make your stay a memorable one.

Middleburg has a humid subtropical climate, with average summertime temperatures fluctuating between 65 ºF and 85 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Middleburg vacation rental and organize your getaway for whenever you like.

What are the best large family vacation rentals in or near Middleburg?

It's always more fun when you share the great times with the people that are closest to your heart. Whether you're planning a family catch-up or getting away with friends, we'll have a large vacation rental to suit your needs. Here are two of our best in and around Middleburg:

  • Around 10 miles to the northwest of Middleburg, "Breathtaking Views With An Indoor Private Pool" has 6 bedrooms and sleeps up to 14 guests. It's equipped with a range of amenities, including outdoor furniture and a microwave oven.
  • "Maple Hill Farm Within Minutes Of Vineyards" is also a top pick for families. It's about 4 miles to the north of Middleburg, has 4 bedrooms and accommodates up to 12 guests. Handy amenities here include a fridge and a microwave oven.

If you're looking for family-friendly attractions around the area, you won't have to go far. Dulles Sportsplex, Claude Moore Park Recreation Center and Panther Family Fun Center promise lots of fun for both adults and kids.

Can I find family cabin rentals in or near Middleburg?

Time spent with family is priceless, which is why we'll help you find a place where you can truly connect. Book one of these family cabin rentals in or near Middleburg and create wonderful memories with the ones you love the most:

  • "Rebels Rest - Mountaintop Cabin With Enchanting Sunset Views" - Approximately 15 miles north of central Middleburg, this family-friendly getaway offers amenities like coffee and tea making facilities and a DVD player.
  • "Blue Ridge Getaway - Mountaintop Cabin With Sunset Views" - Another terrific option, this property comes with a dining table, towels and more. You'll find it around 16 miles to the north of Middleburg.

For more options, use the search bar at the top of the page and adjust the filters to find the Middleburg vacation rental that's perfect for your needs.