Photo by Stephanie Sutton

Middleburg vacation rentals

We found 437 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Middleburg that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. You're sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Middleburg

Showing deals for:Jun 12 - Jun 19

Image gallery for Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Bay window view from living room
10 out of 10, Exceptional, (76 reviews)
Exceptional
(76 reviews)

Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Linden

9% off
Price is $483
$3,380 for 7 nights
All fees included
Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Middleburg

Why visit Middleburg

  • Outdoor Adventures: Enjoy activities like horseback riding and hiking in stunning natural settings.
  • Historic Exploration: Discover rich history through local historic houses and sites.
  • Charming Neighborhoods: Explore family-friendly neighborhoods with vibrant community vibes.
  • Local Cuisine: Savor delicious, locally-sourced dishes at charming eateries.
  • Cozy Accommodations: Relax in delightful vacation rentals, including cottages and cabins, perfect for unwinding.

Popular types of accommodation in Middleburg

If you're considering a getaway in Middleburg, you'll find a range of fantastic vacation rentals to suit your needs. The most popular options include houses, charming cottages, and cozy cabins. Look for ideal house rentals featuring spacious living rooms, air conditioning for comfort, and even a hot tub to unwind after a day of adventure. Experience all that Virginia has to offer with a stay in one of our delightful Middleburg vacation rentals.

  • Houses: The top choice for visitors to Middleburg, offering spacious and comfortable accommodations for families or groups.
  • Cottages: A charming and cozy option, perfect for a romantic getaway or a peaceful retreat in the countryside.
  • Cabins: Ideal for nature enthusiasts, these rustic abodes provide a serene escape surrounded by beautiful landscapes.
  • Apartments: Convenient and versatile, apartments are great for those seeking a home-like feel during their stay.
  • Chalets: A unique lodging experience, chalets combine comfort with a touch of alpine charm.**

Top attractions in and around Middleburg

Middleburg, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and various attractions. Explore urban parks, national state parks, and historic houses that cater to families and city explorers alike. Whether you're traveling solo, with family, or as a couple, Middleburg promises an unforgettable experience filled with natural beauty and cultural heritage.

  • Red Fox Fine Art: Immerse yourself in the local art scene at this charming gallery in Middleburg, featuring a diverse collection of contemporary and traditional works that reflect the region's rich culture and heritage.
  • Glenwood Park: Experience the thrill of horse racing at Glenwood Park, where you can enjoy exhilarating races in a vibrant atmosphere filled with sportsmanship and adventure, perfect for both seasoned fans and newcomers.
  • Aldie Mill Historic Park: Just 5 miles from Middleburg, this urban park offers a serene escape with family-friendly activities, scenic trails, and the historic Aldie Mill, making it an ideal spot for outdoor exploration and relaxation.

Things to do recommended for couples

Middleburg offers a charming escape for couples. Enjoy a scenic wine tasting tour at local vineyards, explore the quaint shops downtown, or take a romantic horseback ride through the picturesque countryside. Don't forget to savor a candlelit dinner at a cozy restaurant, perfect for creating lasting memories.

Things to do recommended for families

Families can explore the beautiful trails at the nearby Appalachian Trail, visit the charming shops in downtown Middleburg, or enjoy horseback riding at local stables. Don't miss the chance to take a scenic drive through the picturesque Virginia countryside for stunning views and photo opportunities.

Things to do recommended for groups

Groups visiting Middleburg can enjoy wine tastings at nearby vineyards, explore the charming historic district with boutique shopping, and take guided horseback rides through the beautiful Virginia countryside. Don't miss the chance to savor local cuisine at cozy restaurants and experience the region's rich equestrian culture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Middleburg

When traveling with a group, family, or pets, or if you're seeking extended stays, it's important to set your priorities for filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Middleburg with a group: Think about how many bedrooms you require and the amenities you desire, such as a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Middleburg with young kids: Traveling with young children can be demanding. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Middleburg: For many, a family vacation isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Middleburg: If you're searching for vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Middleburg

Discover the charm of Middleburg, Virginia, where outdoor adventures meet stunning scenery. Enjoy a relaxing getaway filled with rich history and friendly locals. Explore nearby neighborhoods that offer a family-friendly atmosphere and vibrant community vibes. From horseback riding through picturesque landscapes to savoring local cuisine, Middleburg promises a memorable experience for every traveler. Immerse yourself in the beauty of this magnificent destination and uncover the best of what this lovely region has to offer.

  • Ashburn: Located 14 miles from Middleburg, Ashburn is a lively city that offers a mix of family-friendly activities and urban experiences. Visitors can explore a variety of shopping centers and malls, perfect for picking up local goods or enjoying a meal. The area is also known for its recreational spaces, ideal for outdoor activities. Notable attractions include scenic lakes and the nearby national state park, which provide opportunities for hiking and nature exploration. For those attending business events, Ashburn features several event conference venues, making it a convenient spot for both leisure and work.
  • Leesburg: Also situated 14 miles from Middleburg, Leesburg is a charming city rich in history and modern amenities. Families and business travelers alike will appreciate the vibrant shopping centers and recreational areas that cater to a variety of interests. Enjoy leisurely walks along the picturesque streets or take a break at the local parks. Leesburg's close proximity to a national state park and various event conference venues enhances its appeal, offering both natural beauty and cultural engagement for visitors.
  • Dulles: Just 15 miles from Middleburg, Dulles is a quaint village that provides a peaceful atmosphere while still being close to urban conveniences. Travelers can discover shopping centers and educational venues, making it a great stop for families and business visitors. Dulles features urban parks that are perfect for relaxation and outdoor activities. The nearby national state park and event conference venues further enrich the travel experience, ensuring that guests can enjoy both nature and organized events during their stay.

Best time to go to Middleburg

If you're planning a trip to Middleburg, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.4°F (0.2°C)Light RainMostly SunnySlightly LowSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnySlightly LowSlightly Low
March43.2°F (6.2°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.3°F (17.4°C)Light RainMostly SunnyAverageAverage
June71.8°F (22.1°C)Light RainMostly SunnyAverageSlightly High
July77.0°F (25.0°C)Light RainMostly SunnySlightly HighSlightly High
August74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
September68.2°F (20.1°C)Light RainMostly SunnySlightly HighAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
December37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can often lead to better prices, as they tend to vary. Additionally, opting for an extended stay can result in significant savings. To help you find the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer has its perks. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin your earning journey.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume planning from where you last stopped, or organize your travel plans. You'll find your saved or booked properties neatly categorized into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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—perfect for a relaxing getaway.

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.

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.

Transportation options to and around Middleburg

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

Frequently asked questions

What is the best area to stay in Middleburg, Virginia, United States of America when booking a vacation rental?
When looking to book a vacation rental in Middleburg, Virginia, the historic downtown area is an excellent choice. This charming neighborhood is not only picturesque but also rich in history, making it a delightful base for your stay. You'll find a variety of vacation rentals, ranging from cozy cottages to elegant inns, providing options for different preferences and budgets.

One of the highlights of staying in this area is the proximity to wineries and horse country, which are central to the region's identity. You can easily visit local vineyards to enjoy tastings and tours, or explore the scenic trails that showcase the beautiful Virginia countryside. Additionally, the National Sporting Library & Museum is nearby, offering a fascinating insight into the equestrian and sporting culture that defines Middleburg.

Another fantastic neighborhood to consider is the surrounding countryside, where you can experience the tranquility of rural Virginia. Here, you'll discover lovely farmhouses and spacious properties that offer a peaceful retreat. The area is also home to stunning landscapes, ideal for outdoor activities such as hiking or horseback riding.
How much does it cost to rent a vacation home in Middleburg?
Prices for vacation rentals in Middleburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middleburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middleburg vacation house rentals?
You can find great discounts on house rentals in Middleburg on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Middleburg?
In Middleburg, vacation houses are the most popular rental choice, with around 11 available throughout the picturesque town. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable home base. Additionally, several cottages and apartments can be found in the area, providing a variety of options for travelers. Cottages often feature charming, rustic designs with outdoor spaces for enjoying the surrounding countryside, while apartments cater to those looking for a more compact and convenient stay.
Are there any family house rentals in Middleburg?
In Middleburg, Virginia, there are numerous family-friendly house rentals available—specifically around 16 options throughout the area. This charming town, known for its equestrian culture and scenic countryside, offers a variety of accommodations suitable for families. Many of these homes feature spacious living areas, full kitchens great for preparing family meals, and outdoor spaces where children can play and explore.

Visitors will also find amenities like Wi-Fi and air conditioning, ensuring a comfortable stay. Nearby attractions include the quaint shops and restaurants of downtown Middleburg, as well as opportunities for horseback riding and hiking in the surrounding hills.
Can I rent a vacation home with a pool or hot tub in Middleburg?
In Middleburg, Virginia, there are several vacation homes available for rent that feature pools or hot tubs, providing a superb retreat for relaxation. The town is situated in a picturesque setting, surrounded by rolling hills and beautiful countryside, making it an appealing destination for those seeking a peaceful getaway. Many of these rentals come with a variety of amenities, such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ensuring comfort and convenience for travelers.
Can I find long-stay vacation rentals in Middleburg?
A long-stay vacation rental in Middleburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Middleburg?
In Middleburg, Virginia, there are several pet-friendly house rentals available, offering a superb blend of comfort and convenience for travelers with furry companions. Many of these rentals are designed to accommodate pets, ensuring a welcoming environment for your four-legged friends. Travelers can expect amenities such as spacious yards for play, fully equipped kitchens, and cozy living spaces that make it easy to relax after a day of exploring the charming town.

The area around Middleburg is rich in scenic beauty and outdoor activities. With its picturesque landscapes, guests can enjoy nearby parks and trails that are ideal for walking dogs or simply enjoying the natural surroundings. The quaint historic downtown area is also pet-friendly, with several shops and cafes welcoming pets, making it easy to explore the local culture without leaving your pet behind.
Are there any remote work vacation rentals in Middleburg?
In Middleburg, Virginia, there are several remote work-friendly vacation rentals available, with around 18 options to choose from. These properties cater to those looking to balance work and leisure, often providing essential amenities for productivity. Expect accommodations that include reliable Wi-Fi, dedicated workspaces with desks and chairs, and some may even offer printers for added convenience.

The charming town of Middleburg is known for its rich equestrian culture and beautiful countryside, making it an appealing location for remote work. After a day of work, you can explore local attractions, including historic sites, boutique shops, and delightful dining options. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middleburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middleburg with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Middleburg?
In Middleburg, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios for enjoying the scenic surroundings. Many rentals also offer desks for those needing a dedicated workspace, as well as porches or lanais that provide a relaxed area to unwind. Additionally, air conditioning is commonly available, ensuring comfort during warmer months.
When is the best time to visit Middleburg for a vacation rental?
The best time to book a vacation rental in Middleburg is during the peak season from July to September. This vibrant period attracts travelers eager to experience the charm of Virginia's horse country. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, visitors can enjoy outdoor activities such as horseback riding, vineyard tours, and scenic hikes in the surrounding countryside.

July stands out as the most popular month in Middleburg, offering a lively option filled with local events and activities. The area bursts to life with farmers' markets, art festivals, and opportunities to explore the historic downtown area. It's a great time for those who appreciate the blend of adventure and leisurely exploration.

If you're looking for a more budget-friendly option, consider visiting in January, when you can take advantage of quieter streets and lower rental rates. While the weather can be chilly, averaging in the low 30s to mid-40s Fahrenheit, this month offers a unique chance to enjoy the area's winter beauty and perhaps even some peaceful snow-draped landscapes.
How early should I book a Middleburg vacation rental?
Book your Middleburg vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middleburg, Virginia, United States of America?
In Middleburg, Virginia, visitors can explore a variety of attractions that showcase the area's rich history and stunning natural landscapes. The historic downtown area features charming boutiques, art galleries, and restaurants that reflect the local culture and culinary scene. Nearby, the National Sporting Library & Museum offers a glimpse into the equestrian and sporting heritage of the region, making it a must-visit for enthusiasts.

For those who enjoy outdoor activities, the surrounding countryside is dotted with beautiful vineyards and wineries, where travelers can sample local wines and enjoy scenic views of the Blue Ridge Mountains. The area is also known for its equestrian events, and visitors can often catch a glimpse of horse shows or polo matches at facilities like the Bull Run Hunt Club.

Additionally, exploring the nearby Shenandoah National Park offers opportunities for hiking, wildlife viewing, and breathtaking vistas.
Can I change or cancel my Middleburg home rental booking on Vrbo?
To find Middleburg vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middleburg vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas