Middleburg holiday lettings

We found 427 holiday rentals — enter your dates for availability

Discover a selection of 12 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.

Holiday rentals with weekly discounts - Middleburg

Showing deals for:13 Mar - 20 Mar

Image gallery for Family Reunion Escape: Warm 3BR Chalet

Private kitchen
10 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Family Reunion Escape: Warm 3BR Chalet

Harpers Ferry, WV

7% off
Price is £1,456
for 7 nights, 1 chalet
£208 per night
includes taxes & fees
Family Reunion Escape: Warm 3BR Chalet

Find spaces that suit your style

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 (1.7 mi / 2.8 km)
  • Cana Vineyards and Winery (3.7 mi / 5.9 km)
  • Quattro Goomba's Winery (6.5 mi / 10.4 km)
  • Bull Run Country Club (8.3 mi / 13.3 km)
  • Stone Tower Winery (8.5 mi / 13.7 km)
  • RdV Vineyards (10 mi / 16.1 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:

  • Glenwood Park (2.7 mi / 4.4 km)
  • Aldie Mill Historic Park (5.1 mi / 8.2 km)
  • Ashburn Park (14 mi / 22.5 km)
  • Shenandoah Lake Beach (17.2 mi / 27.7 km)
  • Frying Pan Farm Park (17.6 mi / 28.3 km)
  • Bull Run Regional Park (18.8 mi / 30.2 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 best area to stay in Middleburg when booking a holiday rental?
When considering a holiday rental in Middleburg, Virginia, the most appealing area to stay in would be the historic district. This charming neighbourhood is steeped in rich history and offers an inclusive setting, making it ideal for those looking to immerse themselves in the local culture. Here, you will find a delightful array of quaint shops, art galleries, and restaurants, all within walking distance. A great attraction in this area is the National Sporting Library & Museum, which celebrates the history of equestrian sports and offers fascinating exhibitions.

Another wonderful option is the countryside surrounding Middleburg, where you can discover picturesque landscapes and vineyards. This region is superb for those seeking tranquility and the chance to explore the stunning Virginia countryside. Popular activities include wine tasting at local vineyards and enjoying scenic hikes along the nearby trails. While the number of properties in this area may vary, there are typically a good selection of charming cottages and spacious homes available for rent, suiting various group sizes and preferences.
How much does it cost to rent a holiday home in Middleburg?
Prices for holiday 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 holiday 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 holiday rental accomodation in Middleburg?
In Middleburg, holiday houses are particularly popular, with several options available throughout the charming town. These properties often boast spacious layouts with multiple bedrooms, fully equipped kitchens, and inviting outdoor spaces where guests can relax and enjoy the picturesque countryside. Many are located near local attractions such as the historic Middleburg Museum and various wineries, offering an authentic taste of the region. Additionally, there are also several cottage and apartment rentals, providing a range of choices for travellers looking for a more intimate or compact stay.
Are there any family house rentals in Middleburg?
In Middleburg, Virginia, families will find a variety of holiday rentals, with around 15 options available. This charming town, known for its equestrian culture and picturesque landscapes, offers accommodations in several neighbourhoods, each providing a great experience. Many properties feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces that are great for children to play in.
Can I rent a holiday home with a pool or hot tub in Middleburg?
In Middleburg, Virginia, there are several holiday homes available for rent that feature pools or hot tubs, making it a great choice for those seeking relaxation and leisure. This charming town, known for its picturesque landscapes and equestrian culture, offers a variety of rental options. Many properties come with amenities such as private pools, outdoor seating areas, and well-equipped kitchens, superb for both family gatherings and intimate getaways.
Can I find long-stay holiday rentals in Middleburg?
A long-stay holiday rental in Middleburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middleburg?
In Middleburg, Virginia, there are several pet-friendly house rentals available, with around ten options for travellers to choose from. This charming town, known for its picturesque countryside and equestrian culture, offers holiday rentals that often feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families and those travelling with pets.
Are there any remote work holiday rentals in Middleburg?
In Middleburg, Virginia, there are numerous remote work holiday rentals available, with around 19 options to choose from. This picturesque town, known for its historical charm and beautiful countryside, offers properties that cater specifically to remote workers. Many of these rentals feature dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment. Amenities such as Wi-Fi are standard, allowing for seamless connectivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middleburg holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Middleburg with parking available—perfect for families or travellers 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 rental amenities typically include modern conveniences that enhance the stay experience. Many holiday rentals offer essentials such as microwaves, dishwashers, and cookware, making it easy for guests to prepare meals during their visit. Refrigerators are also commonly found, allowing travellers to store food and drinks conveniently.
When is the best time to visit Middleburg for a holiday rental?
The best time to visit Middleburg for a holiday rental is during the peak season from July to September. This vibrant period attracts travellers keen to experience the charm of Virginia's horse country, where picturesque landscapes and outdoor activities abound. With warm temperatures averaging around 26 to 30 degrees Celsius, it's ideal for exploring the area's historic sites, vineyards, and scenic trails.

July, in particular, stands out as the most popular month, bustling with events such as summer festivals and outdoor concerts. The lively atmosphere makes it an excellent time to engage with local culture while enjoying the natural beauty that surrounds you. Whether you're keen to take leisurely strolls through the quaint town or indulge in wine tastings at nearby vineyards, there's plenty to keep you entertained.

For those seeking a more budget-friendly option, visiting in January offers a quieter experience. While temperatures can dip to around 1 to 5 degrees Celsius, the winter months provide an opportunity to enjoy Middleburg's serene landscapes, superb for cozying up in a charming B&B or exploring local shops without the crowds.
How early should I book a Middleburg holiday rental?
Book your Middleburg holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middleburg?
In Middleburg, Virginia, visitors can enjoy a range of attractions that highlight the area's rich history and stunning natural beauty. The historic downtown area features charming boutiques and restaurants, giving travellers a taste of local culture. Nearby, the National Sporting Library & Museum is a must-visit for those interested in equestrian history and the sporting life of Virginia.
Can I change or cancel my Middleburg home rental booking on Vrbo?
To find Middleburg holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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 holiday ideas