Middleburg holiday rentals

We found 443 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:20 Nov - 27 Nov

Welcome to your cooking retreat - Thermador Column Fridge and Freezer, Gas Stove, Huge Kitchen Sink, Coffee and Hot Coco Station and an Austrian Tile Stove
The deck features ~900 sq ft from the master bedroom to the kitchen and panoramic views of the vineyard and opposing ridge line. Comfortable seating for the whole group!
Everything you could want for a fun family or friend getaway! Multiple firepits, Lots of seating on the deck and around the pool.
15' tall Holiday tree will be up from Thanksgiving to late January. It really is a sight to see!
Exceptional
(58 reviews)

​Vinewood Estate | 10-Acre Luxury Spa & Vineyard Retreat

Purcellville

8% off
AU$22,083
for 7 nights, 1 chalet
AU$3,155 per night
includes taxes & fees
​Vinewood Estate | 10-Acre Luxury Spa & Vineyard Retreat
Cozy family room at Christmas time.
Rest & Relaxation & a glass of tea right here!
Fully equipped kitchen
Grab your poles and head for the the dock and the well stocked fishing pond.
Exceptional
(158 reviews)

Hidden Hollow Farm - Pool; Game Rm; Sleeps 26, 45 min. to DC, Weddings/Corporate

Warrenton

8% off
AU$10,033
for 7 nights, 1 room
AU$1,433 per night
includes taxes & fees
Hidden Hollow Farm - Pool; Game Rm; Sleeps 26, 45 min. to DC, Weddings/Corporate
Private kitchen
Interior
Room
Bedroom #1 with queen bed and full bathroom
Exceptional
(22 reviews)

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Bluemont

8% off
AU$4,654
for 7 nights, 1 cabin
AU$665 per night
includes taxes & fees
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Main Kitchen
Sunroom
Breakfast Area 1
Gruner Bungalow
Exceptional
(108 reviews)

Gruner Bungalow at Tranquility Farm & Winery

Purcellville

12% off
AU$20,461
for 7 nights, 1 home
AU$2,923 per night
includes taxes & fees
Gruner Bungalow at Tranquility Farm & Winery
Exterior
Living area
Property grounds
Very good
(7 reviews)

Premier property(s) sleeps 36..close to Great Meadow Gold Cup Access

Warrenton

12% off
AU$14,840
for 7 nights, 1 home
AU$2,120 per night
includes taxes & fees
Premier property(s) sleeps 36..close to Great Meadow Gold Cup Access
Living room/dining room from stairway landing. French doors to stone patio.
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Interior
Outdoor dining
Exceptional
(113 reviews)

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704

Leesburg

16% off
AU$4,208
for 7 nights, 1 home
AU$601 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Exterior detail
Terrace/patio
Interior
Dining
Exceptional
(45 reviews)

Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues

Bluemont

8% off
AU$5,016
for 7 nights, 1 home
AU$717 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Extra-large mirror and vanity in the 'Purple Rain' room.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
The Kitchen Nook offers additional seating, and a cozy place to read.
Gather and enjoy meals in the spacious, fully stocked kitchen.
Exceptional
(6 reviews)

The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm

Waterford

8% off
AU$5,162
for 7 nights, 1 room
AU$737 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
Kitchen and dining room
Screened in porch with fans
Family room
Stairs to 2nd floor
Exceptional
(5 reviews)

New - The Farmhouse at 1702!

Delaplane

9% off
AU$4,007
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
New - The Farmhouse at 1702!
Interior
Exterior
Property grounds
Interior
Exceptional
(18 reviews)

Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline

Front Royal

12% off
AU$3,901
for 7 nights, 1 cabin
AU$557 per night
includes taxes & fees
Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline
Dining
Property grounds
Property grounds
Living area
Exceptional
(27 reviews)

Apple Mountain Retreat

Linden

12% off
AU$1,831
for 7 nights, 1 apartment
AU$262 per night
includes taxes & fees
Apple Mountain Retreat
Property grounds
Property grounds
Interior
Interior
Exceptional
(26 reviews)

Historic Mountain Cottage at Blue Ridge Overlook

Bluemont

8% off
AU$5,033
for 7 nights, 1 home
AU$719 per night
includes taxes & fees
Historic Mountain Cottage at Blue Ridge Overlook
Primary bedroom with entrance to the kitchen on right and bathroom on left.
Brick patio with mid-1800s brick smokehouse that is on the property.
Primary queen bedroom
Kitchen with refrigerator, microwave, air fryer, toaster, & Keurig with pods
Exceptional
(76 reviews)

Historic 2-Bedroom in Old Town Warrenton, Virginia

Warrenton

8% off
AU$1,856
for 7 nights, 1 apartment
AU$265 per night
includes taxes & fees
Historic 2-Bedroom in Old Town Warrenton, Virginia
Private kitchen
Property grounds
My home from the road.
Outdoor dining
Exceptional
(12 reviews)

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

8% off
AU$2,460
for 7 nights, 1 apartment
AU$351 per night
includes taxes & fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Living area
Exterior
Exterior
Dining
Exceptional
(72 reviews)

Storybook cottage on Leesburg's most historic block — walk to everything

Leesburg

8% off
AU$5,678
for 7 nights, 1 home
AU$811 per night
includes taxes & fees
Storybook cottage on Leesburg's most historic block — walk to everything

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, 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 (1.7 mi / 2.8 km)
  • Quattro Goomba's Winery (6.5 mi / 10.4 km)
  • Stone Tower Winery (8.5 mi / 13.7 km)
  • RdV Vineyards (10 mi / 16.1 km)
  • Bluemont Vineyard (10.4 mi / 16.7 km)
  • Brambleton Regional Park Golf Course (10.6 mi / 17.1 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:

  • 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)
  • Ben Lomond Manor House & Old Rose Garden (17.5 mi / 28.2 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 looking for the best area to stay in Middleburg, Virginia for a holiday rental, the charming historic district is a top choice. This area is rich in character, featuring beautifully preserved buildings and a quaint, small-town atmosphere. Visitors will find a delightful array of shops, galleries, and eateries, making it a convenient and enjoyable base for exploring the region.One of the standout attractions in the historic district is the National Sporting Library & Museum, which offers a fascinating insight into the history of equestrian sports and rural life. Additionally, nearby, you can explore the stunning landscapes of the surrounding countryside, which is ideal for outdoor activities such as hiking, horseback riding, and wine tasting at local vineyards.Another appealing neighbourhood is the area surrounding the local wineries and vineyards. Staying here allows guests to immerse themselves in the beautiful Virginia wine country, with several renowned wineries just a short drive away. This picturesque region provides not only scenic views but also hosts various events and tastings throughout the year, making it a delightful experience for wine enthusiasts.
What is the most popular type of holiday rental accomodation in Middleburg?
In Middleburg, holiday houses are the most popular type of holiday rental, with approximately 44 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and large outdoor spaces, making them ideal for families or groups looking to enjoy the charming countryside. Additionally, there are about 20 cottages that provide a quaint and cosy atmosphere, superb for those seeking a more intimate setting amid the picturesque landscapes. For travellers looking for a more compact option, around 12 apartments are also on offer, typically including essential amenities such as kitchen facilities and comfortable living areas.
Are there any family house rentals in Middleburg?
In Middleburg, Virginia, families will find a variety of holiday rentals available—there are 16 properties suited for group stays. The charming town offers a picturesque setting with its historic architecture and beautiful countryside, making it an excellent destination for family gatherings. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play and explore. Amenities such as Wi-Fi and air conditioning ensure a comfortable visit.Nearby attractions include the stunning vineyards and wineries of Loudoun County, where families can enjoy scenic tours and tastings. Additionally, the area boasts numerous parks and hiking trails, allowing for outdoor adventures.
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 and hot tubs. This charming town, known for its picturesque countryside and equestrian culture, offers a selection of properties that cater to those seeking relaxation and outdoor enjoyment. Many rentals come equipped with private pools, hot tubs, and spacious outdoor areas, superb for family gatherings or peaceful retreats.Travellers can expect amenities such as well-appointed kitchens, comfortable living spaces, and often beautiful views of the surrounding landscape. The area also boasts proximity to local vineyards and historical sites, making it an ideal destination for both leisure and exploration.
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 looking to bring their furry companions along. This charming town, known for its picturesque landscapes and equestrian culture, offers a variety of holiday homes that often include amenities such as spacious gardens, modern kitchens, and comfortable living areas, ideal for families or groups. Many of these rentals are situated within close proximity to the scenic countryside, allowing for leisurely walks and outdoor adventures with pets.Moreover, Middleburg's location in the heart of Virginia's wine country provides access to numerous vineyards and wineries that welcome pets, enhancing the overall experience for pet owners. The town itself boasts quaint shops and pet-friendly cafes, making it a delightful destination for those looking to explore while accompanied by their pets.
Are there any remote work holiday rentals in Middleburg?
In Middleburg, Virginia, there are a variety of remote work holiday rentals available, with around 72 options to choose from. This picturesque town, known for its charming equestrian culture and historic sites, provides a tranquil setting for those looking to combine work and leisure. Many properties come equipped with essential amenities tailored for remote work, including reliable Wi-Fi, dedicated workspaces with desks and chairs, and some even feature printers for added convenience.Visitors can enjoy the surrounding countryside, with opportunities to explore local wineries and historic landmarks such as the National Sporting Library and Museum. Properties often offer comfortable living areas, full kitchens for self-catering, and outdoor spaces to relax after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Middleburg?
In Middleburg, popular rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces like decks or patios that provide a lovely setting for relaxation. Many properties also feature desks, accommodating those who may need to work or study during their stay. Porches or lanais are common as well, offering additional outdoor spaces to enjoy the charming countryside. Air conditioning is a sought-after feature, ensuring comfort during warmer months.
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 welcomes travellers eager to explore the lush Virginia countryside, partake in outdoor activities, and experience the charming local culture. With warm summer temperatures averaging between 20 to 30 degrees Celsius, it's ideal for enjoying leisurely strolls through the picturesque town or exploring the scenic vineyards and horse farms that the region is famous for.July stands out as the most popular month, offering a lively option filled with events and festivals. Visitors can indulge in wine tastings, attend local fairs, or simply enjoy the vibrant community spirit that fills the air. The weather is superb for outdoor excursions, whether you're hiking along the nearby trails or picnicking in one of the many beautiful parks.For those seeking a more budget-friendly option, consider planning your visit in January. While it's considered low season, the winter months bring a unique charm to Middleburg, with picturesque landscapes and fewer crowds. This time can be superb for cosy getaways, where you can enjoy fireside chats in charming cafés or explore local shops at your leisure.Ultimately, your ideal time to visit Middleburg depends on whether you prefer the bustling summer atmosphere filled with activities or the tranquil beauty of winter.
What are the top attractions in Middleburg?
In Middleburg, Virginia, visitors can enjoy a charming blend of history and natural beauty. The town is known for its picturesque Main Street, lined with quaint shops, art galleries, and delightful eateries that reflect the local culture. A must-visit is the National Sporting Library & Museum, which showcases the heritage of equestrian sports in America and hosts various events throughout the year.For those who appreciate the outdoors, the surrounding Virginia countryside offers stunning views and opportunities for hiking and horseback riding. The nearby Merrybrook Farm and the scenic trails of the Appalachian Mountains provide ample chances for exploration. Additionally, wine enthusiasts can explore the many vineyards and wineries in the region, where tastings and tours are often available, adding to the area's appeal.
Are all fees included in the Middleburg holiday homes prices shown on Stayz?
Stayz 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.
Are there any Middleburg holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Middleburg holiday homes?
You can find great discounts on holiday homes in Middleburg on Stayz, 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.
Can I change or cancel my Middleburg holiday home booking on Stayz?
To find Middleburg holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middleburg?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Middleburg holiday home?
Book your Middleburg holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middleburg?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Middleburg to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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