Airbnb your place

Holiday rentals in Middleburg

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Middleburg

  • Nightly prices starting at

    Middleburg holiday rentals start at £163 per night before taxes and fees

  • Verified guest reviews

    Over 30 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Middleburg rentals

  • 5 Average rating

    Middleburg stays are highly rated by guests – averaging 5 out of 5!

Top-rated holiday rentals in Middleburg

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
A well-maintained sign for Tonka Farm is positioned at the entrance along a gravel driveway. Lush green grass surrounds a neatly trimmed shrub. Black wooden fencing lines the pathway, leading to a serene and inviting country setting.
Farm stay in Middleburg
4.97 out of 5 average rating, 102 reviews

Retreat to horse country!

Enjoy your visit while staying in a private country setting complete with a swimming pool and gardens creating a resort like feel. This beautiful family farm includes an English style apartment with large windows, gas fireplace, 1.5 bathrooms, 1 large bedroom with king size bed. An open concept living space, access to the pool a large & outdoor seating and dinning. Minutes to vineyards, Salamander, Goodstone, Upperville and Shadow Creek in Purcellville! Please read “other details” for pet info😊

Top guest favourite
The exterior of the cabin is showcased with a green metal roof and rustic wooden siding. Gentle outdoor lighting highlights the structure while lush greenery surrounds the gravel driveway, leading to an inviting entrance. The spacious yard features landscaped gardens and a welcoming atmosphere.
Cabin in Aldie
4.99 out of 5 average rating, 152 reviews

Oatlands Creek cabin

Welcome to Oatlands Creek, the ideal getaway for relaxing and exploring Old Town Leesburg, Aldie, and Middleburg. Set on 22 private acres, driving up you’ll be greeted by horses in the neighborhood. This beautifully renovated cabin blends rustic charm with modern comforts, featuring 4 spacious bedrooms, an open dining and living space, theater room, game room, and hot tub. Whether you’re here for wine country, family visits, bachelorette parties, or work, this cabin is the perfect spot for you.

Top guest favourite
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guest house in Middleburg
5.0 out of 5 average rating, 140 reviews

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

Top guest favourite
An open-concept kitchen and dining area features modern appliances and a spacious island countertop. A large dining table is surrounded by sleek chairs. Natural light pours in through multiple windows, highlighting the warm wood floors and neutral color palette.
Home in Middleburg
4.96 out of 5 average rating, 217 reviews

Modern Home on Middleburg Equestrian Farm

Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.

Top guest favourite
A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.
Cottage in Marshall
4.91 out of 5 average rating, 141 reviews

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. Please be mindful this property is near a train track, charming!

Top guest favourite
A charming cottage is situated within a natural setting, featuring light-colored siding and a shingled roof. The entrance is highlighted by a vibrant orange door, flanked by multiple windows. A stone pathway leads to the front steps, surrounded by a well-kept lawn and gentle landscaping.
Cottage in Middleburg
5.0 out of 5 average rating, 90 reviews

Middleburg Bliss!

Treat yourself to a peaceful getaway in our cozy guest cottage! Nestled on 10 acres of serene, park-like grounds, our private retreat offers peace and tranquility just 10 minutes from charming Middleburg. Enjoy natural beauty and countryside sounds while exploring nearby award-winning wineries, breweries, and historic towns. Enjoy great privacy with us nearby if needed. Whether you’re here to unwind or embark on local adventures, our cottage is the ideal home base for your Middleburg escape.

Guest favourite
An aerial view captures a vibrant organic vegetable garden surrounded by a black wooden fence. The garden features neatly arranged raised beds filled with various plants, along with gravel pathways. A shaded seating area is visible, alongside a shed and open green space beyond.
Guest house in Middleburg
4.95 out of 5 average rating, 102 reviews

Fox Hill Barn Guest Cottage Retreat

Enjoy the lovely setting of this romantic spot in nature, just minutes from the historic charm of Middleburg. Set on a tranquil horse property, this cottage offers a serene retreat amidst rolling pastures and breathtaking views. Whether you're a nature enthusiast, equestrian, remote worker, or seeking a romantic getaway, this is your ideal destination. Enjoy nearby wineries, breweries, scenic trails, and the delightful town of Middleburg—only 3 minutes away. Life is too short. Enjoy!

Guest favourite
The spacious apartment features a cozy sleeping area with a comfortable bed, a dining table set for two, and a sitting area with armchairs. Natural light enters through large windows, illuminating the inviting space with wooden flooring.
Farm stay in Middleburg
4.92 out of 5 average rating, 165 reviews

Self-contained apartment on Organic vegetable farm

Enjoy a relaxing retreat at a genuine sustainable organic vegetable farm. This self-contained apartment is the perfect location for a family get away, or overnight stay whilst visiting the many local wineries and breweries. The farm is located just 5 miles from historic Middleburg, right in the middle of hunt country. See what life is like on a working farm, with seasonal healthy vegetables growing just steps from the door and farm animals grazing outside your window.

Guest favourite
Barn in Middleburg
4.93 out of 5 average rating, 228 reviews

Middleburg Carriage House

Hunt Country charm with modern design and amenities. The rebuilt carriage house overlooks adjacent vineyard and Blue Ridge Mountains. The interior showcases reclaimed materials and wood from the original dwelling. The large flagstone patio offers rolling mountain views where you can enjoy your morning coffee or glass of local wine after a day of winery visits. A two minute drive to historic downtown Middleburg; next to wineries and polo. Enjoy your next getaway!

Top guest favourite
The charming exterior features a light-colored house with a metal roof, framed by well-kept greenery. A bold blue door provides an inviting entrance, while white window shutters accentuate the classic style of the home.
Cottage in Upperville
4.9 out of 5 average rating, 108 reviews

Cozy Country Getaway in the Heart of Upperville

Located in the center of the historic village of Upperville - across from the Hunter's Head Tavern. House is situated on 2.5 acres of beautiful gardens. It feels like an English cottage that dates back to early 1900s and is newly updated. Tall ceilings with tons of light make this house feel very spacious. There are 2 large bedrooms with 3 beds. Upstairs is a large loft with desk area. Parking provides space for 5 vehicles. Dogs are welcome! Wifi available.

Top guest favourite
A modern kitchen features stainless steel appliances, including a washer and dryer. Warm wood shelves display plants and essentials. Natural light fills the space, highlighting the stone wall and wooden dining table with seating for two, creating a welcoming atmosphere.
Flat in Middleburg
5.0 out of 5 average rating, 91 reviews

Middleburg Carriage House Flat Coachman’s Quarters

Welcome to Coachman's Quarters! Experience the charm of yesteryear in this newly renovated, second-floor private unit within a 1930s stone Carriage House. Each room has been thoughtfully curated for your ultimate comfort, featuring a queen-sized bed with your choice of down or alternative bedding, fine linens, full-size appliances, and scenic views from every window. Unwind in the sunroom on the Charleston twin bed for a lazy afternoon nap or a relaxing read.

Top guest favourite
A modern kitchen and living area are showcased, featuring a large central island with seating for six. Two prominent horse portraits hang above the island, while the sleek design is complemented by gold accents and a mix of light and dark tones throughout the space.
Barn in Middleburg
4.98 out of 5 average rating, 111 reviews

The Studio

🐞1 mile from the center of Middleburg, this gem allows you to enjoy the beauty of a gorgeous Middleburg Farm when you stay in this unique tractor barn turned high end luxury studio apartment! This is for the customer who wants to experience country living but does not want to give up any luxury 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property.

Popular amenities for Middleburg holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Middleburg's top sights

Boxwood Estate Winery

45 locals recommend

National Sporting Library

32 locals recommend

Mt Defiance Cidery & Distillery

24 locals recommend

Other great holiday rentals in Middleburg

Guest favourite
Home in Middleburg
4.85 out of 5 average rating, 13 reviews

Hunt Country Stone Cottage

Top guest favourite
The entrance features a charming stone facade, complemented by a white door with decorative glass panels. A horse-shaped door knocker adds a rustic touch, while a lantern illuminates the entryway. Lush green shrubs and a stone pathway enhance the inviting exterior.
Home in Middleburg
4.94 out of 5 average rating, 89 reviews

Peaceful, Authentic Stone Cottage with Cozy Charm

Top guest favourite
A charming house is set against a backdrop of mature trees, with a wide driveway leading to a welcoming entrance. The exterior features a light-colored façade, complemented by a white railing and a sign reading 'Stoney Creek' on a brick pathway.
Home in Middleburg
4.97 out of 5 average rating, 76 reviews

Countryside cottage quiet setting in Middleburg

Top guest favourite
Farm stay in Upperville
5.0 out of 5 average rating, 15 reviews

Farmhouse, pond & paddock views

Guest favourite
Home in Marshall
5.0 out of 5 average rating, 12 reviews

Middleburg Wine Country Retreat on 135 Acres

Guest favourite
Home in Upperville
4.92 out of 5 average rating, 24 reviews

Horse Country | Pool | MNT Views | Full Kitchen

Top guest favourite
The home's exterior features a blend of white siding and stone accents, complementing a metal roof. A welcoming front porch is supported by white columns and is adorned with potted plants and outdoor seating, surrounded by landscaped greenery.
Home in Middleburg
5.0 out of 5 average rating, 31 reviews

Middleburg country home

Top guest favourite
The exterior of Longview House reveals a modern two-story design, featuring large glass doors that open to a welcoming entryway. Stone steps lead up to the entrance, surrounded by lush greenery and natural landscaping.
Cottage in Bluemont
5.0 out of 5 average rating, 57 reviews

Designer Modern Mountain Escape (w/View & Hot Tub)

Frequently Asked Questions

  • What are the best places to stay in Middleburg?

    Middleburg has vacation rentals and bed-and-breakfasts set among scenic vineyards, historic streets, and countryside estates. Many stays blend original architecture with modern comforts, and homes near town square put local dining, shops, and galleries within easy reach.

  • What are the best things to do in Middleburg with kids?

    Families often explore local nature preserves, pick seasonal fruits at nearby farms, or visit equestrian centers for horseback riding. Interactive history museums and outdoor picnics are also popular with younger visitors.

  • What are some of the best things to do in Middleburg?

    You can explore local wineries, stroll through independent boutiques, and visit history museums highlighting regional heritage. Middleburg is also known for its equestrian events, outdoor trails, and art galleries.

  • How is the weather in Middleburg?

    Middleburg has cold winters around 25–46°F (-4–8°C) and warm summers reaching 86–88°F (30–31°C). Spring and fall bring mild temperatures, so layering is suggested, especially if outdoor activities are on your agenda.

  • When is the best time to visit Middleburg?

    Late spring and early autumn are often recommended for comfortable weather, with blooming landscapes or colorful foliage. These seasons also coincide with popular outdoor festivals and equestrian gatherings.

  • What are the best places to visit in Middleburg?

    Frequent favorites include the National Sporting Library & Museum, local vineyards, and historic sites around the town center. Scenic drives and rural lanes reveal countryside views and opportunities for photography.

  • What are some hiking trails in Middleburg?

    Middleburg has access to nature preserves and parks with walking trails that wind through woodlands and open fields. Look for nearby routes with scenic vistas, stream crossings, and opportunities to spot local wildlife.

  • What are some family activities we can do in Middleburg?

    Families can visit interactive museums, try horseback riding at local stables, or enjoy farm tours and seasonal festivals. Outdoor picnics and easy hiking trails are frequently suggested ways to enjoy the landscape together.

  • What are some of the best day trip ideas from Middleburg?

    You can explore nearby small towns known for antiquing, visit Civil War battlefields, or discover larger regional parks with hiking and water activities. Touring additional wineries and art galleries in the surrounding countryside is also popular.

  • Are there any pet friendly accommodations available in Middleburg?

    Middleburg has pet-friendly vacation rentals and inns, especially in countryside settings or near open spaces. Many hosts welcome dogs and share guidance on local walking trails and outdoor cafes.

  • What are some local tips for visiting Middleburg?

    Locals often recommend making reservations at popular wineries and restaurants, especially on weekends. Wear comfortable shoes for strolling historic streets, and check local calendars for equestrian events or seasonal festivals to enhance your visit.

  • What is Middleburg known for?

    Middleburg is known for its equestrian culture, historic architecture, and vibrant wine scene. The town often draws visitors interested in horse events, country markets, and its storied role in regional history.

  • What are the best hidden gems to explore in Middleburg?

    Artisan shops tucked along side streets, lesser-known vineyards, and quiet public gardens are often suggested hidden gems in Middleburg. Locals sometimes mention small museums or heritage properties that highlight community history.

  • What are the best foods to try in Middleburg?

    Middleburg’s dining scene features farm-to-table dishes, local cheeses, and specialty baked goods—regional classics such as fried chicken or seasonal fruit cobblers are frequently suggested. Pairing Virginia wines with locally inspired meals is a highlight for many visitors.

  • What should I bring for a trip to Middleburg?

    Comfortable footwear is helpful for walking around historic streets and countryside trails. Consider packing layers for changeable weather, and bring a compact umbrella or rain jacket, especially if you plan outdoor activities.

  • What is the nightlife in Middleburg like?

    Nightlife in Middleburg is relaxed, centered around wine bars, local pubs, and occasional live music events. Many evenings are spent sharing regional wines or cocktails in cozy, historic venues.

  • What are the most popular events or festivals in Middleburg?

    Equestrian events are a highlight throughout the year, with steeplechase races and horse shows often drawing crowds in spring and fall. Holiday parades, seasonal festivals, and local art fairs offer more ways to experience the vibrant community spirit.

  • Are there family friendly vacation rentals in Middleburg?

    Family-friendly vacation rentals are available in Middleburg, with many homes set up for groups and children. Properties often include yards, spacious living areas, and convenient access to parks or kid-friendly attractions.

Destinations to explore