Do you want to take a break from city life and escape to Virginia’s Loudoun County? Why not make the lovely little town of Middleburg your home for a while? This destination nestles in the southernmost part of the county, and it is characterized by its small population, good quality of life, and slow-paced suburban feel. For leisure, you can visit National Sporting Library & Museum and check out its books and artworks. The town is packed with must-try hangout nooks and dining spots. You can check out Red Horse Tavern, King Street Oyster Bar, and Thaiverse Restaurant Middleburg. If you’re craving coffee and pastries, Cuppa Giddy Up is the place to be. For your upcoming visit, have you chosen accommodation yet? Middleburg has guesthouses in and near the town limits that you might be interested in. Browse through this list of top Airbnb vacation rentals in Middleburg, Virginia.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 29, 2025.
1. The Delft Suite (from USD 671)
Pinterest-savvy holidayers and meticulous travelers will love this tastefully curated Airbnb rental at Van Der Meijden Manor. The Delft Suite is covered in floral wallpaper in muted tones, complemented by natural light. Rustic finishes add charm to the interiors, while up-to-date amenities, from the air-conditioning to the walk-in shower, ensure a convenient stay. The pet-friendly unit also has a kitchen with cookware and cutlery.
This place is also WiFi-ready, making it suitable for business travelers as much as holidayers.
Middleburg, Virginia, United States
5.99 km (3.8 mi) from 50 West VineyardsSuperhost
Accommodates: 4
Top guest reviews
Location:
loved staying at this locationright outside of town and close to polo the location for us was perfectyou can walk easily to mtgreat place- close to town and quite accessiblegorgeous decor primo location and terrific hostsCleanliness:
the unit is in a neat old house clean well decorated and well appointedRead more reviewsAmenities & Room:
beautiful and well-equipped apartment perfect for groups of 2-4 people
Nearby Airbnb vacation rentals
2. Scenic cottage with a picnic area (from USD 766)
An escape to nature is what this waterfront cottage is all about. It has surrounding lush greenery, and guests will love the sight and sound of Goose Creek throughout their stay. Moreover, the accommodation has expansive windows that allow patrons to admire nature in comfort. The living space, dining area, and bathtub even have a view. Outside, there’s a picnic table that invites you to plan a cookout with your loved ones.
This Airbnb rental is also pet-friendly, so feel free to bring your well-behaved pooch along.
Middleburg, Virginia, United States
9.55 km (6.0 mi) from 50 West VineyardsAccommodates: 3
Top guest reviews
Host:
she was super flexible and attentivehost is very accommodating and friendlybarb is a great hostbarb was a great host and responded within minutes to our questions and needsbarbara was very responsive to any questionsLocation:
overall cute placelocation is fantastic: 5 mins drive from middleburgsuch a great place it’s beautiful and in close proximity to town and nearby wineries and restaurants :)close to tons of parks trails and backwoods areas which was perfect with our pupsthe location couldn’t have asked for a better place to stayCleanliness:
very clean and comfortablethe place is very clean and well maintainedthe place was very clean with an updated kitchen and showerthe house is quite spacious and very cleanwell cared for and cleanRead more reviewsAmenities & Room:
the cottage was cozy with a fantastic viewbarb's waterfront cottage at goose creek was the perfect cozy cottagethe top quality furnishings are super comfortable and aesthetically pleasingthis cozy cottage was surrounded with the most wonderful sights and sounds of naturethe living room had an amazing view of the surrounding trees and creek
3. Dreamy English-inspired property (from USD 486)
With an Old English design and gorgeous gardens filled with vibrant blooms, this cottage can make you feel teleported to a dreamy English countryside. It comes with al fresco dining and barbecue equipment for afternoon tea or spontaneous grilling.
Inside the house, you’ll find everything you need, from a workspace to a well-equipped kitchenette. A Keurig coffee maker is available for your daily caffeine fix. With a private backyard, this accommodation has a play area for you and your fur baby.
Middleburg, Virginia, United States
10.3 km (6.4 mi) from 50 West VineyardsAccommodates: 2
Top guest reviews
Host:
sandi was a wonderful host and so helpful during our staysandy and peter are very helpful and communicate very quicklysandi was very informative and responsiveit was such a memorable trip and sandi was an awesome hostvery gracious hosts perfect locationLocation:
ideal location for a middleburg weekendgreat location just outside of middleburgthe location is great for access to middleburg as wellperfect location for a romantic weekend and a winery tourgreat place to stay for trips to middleburgCleanliness:
it was clean and so cutethe cottage is clean cozy and comfortablelovely cottage very clean fully stocked and comfortable bedit is very comfortable extremely clean and the surroundings are gorgeousvery clean thoughtful hosts and perfect locationRead more reviewsAmenities & Room:
the cottage was lovely and comfortable and it was easy to adjust the air temperaturethe cottage was cozy and the perfect place to unwind in the eveningsmattress was comfortable and the cottage was perfect for us for the weekendthe cottage is beautiful cozy comfortable and very much lives up to the photosit was clean air conditioned and the bed/pillows were comfy
4. Charming stone dwelling with modern conveniences (from USD 1297)
How would you like to stay in a charming stone cottage surrounded by rich vegetation for your Virginia holiday? This Airbnb vacation rental features a beautiful interior adorned with natural elements, such as stone finishes, wooden fittings, and plenty of natural light. Modern-day conveniences, including kitchen appliances and WiFi, are ready here. While there’s a stone fireplace, it’s only for the visual aspect and non-operational.
Although you’d find the living room with a wide-screen TV relaxing, wait till you see the outdoor lounge area with a dining table and barbecue equipment.
Middleburg, Virginia, United States
9.94 km (6.2 mi) from 50 West VineyardsAccommodates: 6
Top guest reviews
Host:
host was very accommodating and kindthe homeowners were very responsiveyutao is a great hostshe is very responsiveyutao is an amazing host and the home is spotless and extremely comfortableLocation:
amazing location to visit middleburggreat location just a 2 minute car right outside of downtown middleburgloved the location just minutes from middleburgcharming house close to middleburg and all the attractions of virginia wine and hunt countryif you are ever in need of a place to stay near middleburg i highly recommend itRead more reviewsCleanliness:
this home was clean cozy and well managedinside was clean as a whistle and the beds were incredibly comfortablethe house was very clean in a great location and the host was very communicative and nice
5. Pet-friendly vacation rental (from USD 1099)
If you’re on the hunt for the perfect vacation rental for you and your loved ones, this countryside cottage will suit you well. It can accommodate everyone in the family, including the four-legged ones. Lucky for your fur babies, there’s an expansive grassy lawn waiting for them here.
Two-legged holidayers, on the other hand, will surely be thrilled with the indoor amenities. Air-conditioning, a dedicated workspace, and kitchen necessities are available for their convenience. WiFi is a bonus here. You’ll also appreciate the outdoor coffee area.
Middleburg, Virginia, United States
6.47 km (4.1 mi) from 50 West VineyardsAccommodates: 5
Top guest reviews
Host:
trish the host is so sweet and kind and lightning-fast with her response to any questions we hadpatricia is a great hosthost was very responsive and the guide listing was helpful as to how to use the housethis was the perfect find beautiful house and fabulous hostshe was a super responsive host and the cottage was perfect for usLocation:
perfect location close to downtown middleburggreat location close to downtown middleburg in a beautiful locationonly a few minutes to town yet great countryside locationthe location couldn’t have been betterconvenient location and we really enjoyed the nespresso and wineCleanliness:
very clean comfortable & quiethouse is clean pretty and spaciousthe beds were comfortable and the house was very cleanquiet peaceful clean fabulous hospitality and responsivenessso beautiful clean and comfortable extremely well kittedRead more reviewsAmenities & Room:
two really nice living rooms-one with beautiful views and fireplacehouse was quiet had beautiful natural light and beds were comfythe house was wonderful—the beds were super comfortable—the large kitchen allowed us all to gather aroundthe extra blankets provided were wonderful and the beds were comfythe bathrooms and bedroom are wonderful and the kitchen is fully-equipped
6. The Gate House (from USD 1744)
Welcome to this charming and cozy Airbnb rental called The Gate House, which provides guests with a comfortable and worry-free stay. Here, you have everything you need for cooking, from spacious wooden counters to up-to-date appliances. There’s plenty of indoor and outdoor dining, which are also perfect spots for coffee. On lazy afternoons, you can chill in the living room, read books, or bond with your fur ball in the expansive outdoor space.
For guests arriving with their Teslas, an electric vehicle charger is available.
Middleburg, Virginia, United States
9.55 km (6.0 mi) from 50 West VineyardsAccommodates: 3
Top guest reviews
Host:
host and hostess had wonderful recommendations and were very attentiveperfect place and hostthey were great hosts and we would love to come backthe hosts were a pleasure to meet and easy to interact withthis was the perfect airbnb with the most lovely and welcoming hosts we can't wait to come backLocation:
charming house in a great location in the countrysideperfect location and the gate house was exceptionala great place to get away from the hustle and bustle of the rest of the worldcute and comfortable cottage in a great location connie was very responsive and helpfulconnie was very helpful and the location was greatCleanliness:
the property was amazing very clean and well maintainedthe cottage is completely charming super clean and comfyhad an amazing and relaxing stay the house was clean and cozy and the perfect set up to relaxRead more reviewsAmenities & Room:
the furniture is beautiful and comfortableher cottage is adorable and cozythe cottage is warm and cozy with great spots for reading and gamesthe coziest cutest little cottage in the virginia countrysidea cute cozy cottage wonderfully decorated and great access to the property to get some fresh air
7. Elegant manor with a well-appointed kitchen (from USD 1514)
There is plenty to like about this vacation rental, from its elegant design to its lush surroundings. The interior of this manor will impress you with its bright furnishings, wooden flooring, and cutting-edge appliances.
The kitchen, with stainless steel appliances, is a playground for culinary enthusiasts. With internet access, this accommodation allows you to brush up on your recipe knowledge with the help of YouTube. The six-seater dining set has enough room for you and your vacation buddies. The rest of the pack can take advantage of the De'Longhi Espresso machine while they wait for your gastronomic masterpieces.
Middleburg, Virginia, United States
4.09 km (2.6 mi) from 50 West VineyardsAccommodates: 6
Top guest reviews
Host:
the host was super easy to communicate with and responded quickly to any questions we haddawood was a great host checked in with us to make sure everything was going welldawood was a great host and very easy to communicate with we enjoyed our stayrounding out our experience dawood was a most gracious host and very communicativedawood is an excellent host and he made sure our experience was enjoyableLocation:
the location was perfectgreat location a few minutes from townlocation was great— super close to town and being in walking distance to greenhill was fantasticperfect house and perfect locationthe location is just a few minutes from town with easy access to wineries restaurants and shoppingCleanliness:
smooth checkin process very clean homevery clean though and communication was excellentlinens were clean and comfortablegreat place well kept and cleancomfortable clean convenient and overall a beautiful placeRead more reviewsAmenities & Room:
all of the light and fan switches are labeled which is such a great little detailvery well-equipped and perfect for a cozy weekend with friends
8. Littlefield Cottage (from USD 1045)
Forget about the busy city and escape to this countryside cottage that will immerse you in the beauty of greenery and flora. Upon arrival, you will be greeted by the charming garden space, furnished with al fresco dining and a fire pit area. The interior is fitted with the rest of the necessities, including a well-appointed kitchen, central air-conditioning, and internet access.
Long-term guests will benefit from the in-house washer and dryer. Best of all, the monthly discounts will make your extended stay sweeter.
Middleburg, Virginia, United States
4.04 km (2.6 mi) from 50 West VineyardsAccommodates: 6
Top guest reviews
Host:
host was very helpful with answering questions and providing recommendationsshe was always super responsive and caring throughout the processowner very responsive and helpfuljeannie is a wonderful host - very responsive and helpfuljeannie was very helpful with clear directions and recommendationsLocation:
great location right next to a winery and close to many othersgreat place in a great locationgreat location and a really cute property for a little getaway for a few daysvery peaceful the location is great - close to town and wineries but also privateperfect location as greenhill is walkable and downtown is a short driveCleanliness:
meticulously clean charming well maintained airbnbcute and quaint very clean and modern with lots of charmvery clean and comfortable and it had everything that we neededbeautiful clean enchanting homecomfy beds and linens extremely clean well stocked and the backyard is just so peacefulRead more reviewsAmenities & Room:
the furniture was beautiful and comfortablelittlefield cottage is quite beautiful and cozybeds were super comfortable and the cottage feels private and secludedwe loved our 2-night stay at littlefield cottage the cottage was well-stocked as pictured and extremely clean and cozythe king bed was very comfortable
9. Cozy abode with a fireplace (from USD 1795)
One of the best things about this Airbnb rental is its fantastic location. While near many key points of interest, such as wineries and must-try restaurants, it sits in a peaceful and quiet setting where you can relish relaxation.
If you wish to stay in for the day, you can unleash your culinary prowess in the kitchen, which boasts top-of-the-line cooking appliances. While your family waits for your cooking, they can relax by the fireplace while browsing the web. The living space features a wide-screen TV and leather couches, with enough room for everyone.
Middleburg, Virginia, United States
7.22 km (4.5 mi) from 50 West VineyardsAccommodates: 6
Top guest reviews
Host:
garet was the perfect hostgaret is a great hosthost was easy friendly and easy to communicate withgaret was so welcoming friendly and responsivegaret was so welcoming friendly and responsiveLocation:
the location is great very close to townsuper close to middleburg and local attractionsthe location is great and surroundings beautifulbank barn was fantastic the location was just a few minutes away from downtown middleburg and so peacefulthe perfect location to downtown middleburg and wineriesCleanliness:
very clean and well equipped houseit was extremely clean well stocked and had super comfy bedsplace was clean had enough sheetsthe house was very spacious clean and cozyhouse was clean spacious comfortable and decoratedRead more reviewsAmenities & Room:
beds were also extremely comfortablethe large kitchen allowed for team cooking and the dining table easily accommodated all of usspacious living areas comfortable beds and lots of amenities to help us settle in nicelythe house was beautiful and the king beds with crisp linens were super comfortablebeautiful home; comfortable & relaxing; well stocked
10. High-end haven on a farm (from USD 613)
This property boasts the best of country life and architecture of the city. It is a luxurious Airbnb rental suitable for design-savvy couples on a romantic getaway. Its Pinterest-worthy interiors boast wooden flooring, neutral-colored furnishings, and opulent chandeliers that add elegance to the place. An open kitchen with a spacious breakfast bar waits for you to showcase your cooking skills.
Apart from a stylish home, part of your stay is the experience of farm life. You may explore the property and join guided tours of the farm.
Middleburg, Virginia, United States
8.89 km (5.6 mi) from 50 West VineyardsAccommodates: 2
Top guest reviews
Host:
the host was lovelythe cows coco and cash are adorable and friendlyangela was the nicest host that i have dealt with and her place was impeccableLocation:
beautiful studio with great outdoor space and very close to downtown middleburgRead more reviewsCleanliness:
stylish clean comfortable perfectly situated peaceful and easy to use
Have a slow-paced holiday in Middleburg
With warm, friendly people, a slow-paced feel, and plenty of quality dining spots, Middleburg has all the making of the perfect getaway destination. If you’re planning a visit, choose a stay from this list of top Airbnb vacation rentals in Middleburg, Virginia.
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