Places to stay in Middleburg, VA

12 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Middleburg, VA place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

12 Best places to stay in Middleburg, VA

Best family friendly Middleburg, VA lodging

Among the 4 accommodations in Middleburg, VA, here are the 4 best for families

Middleburg Carriage House - Middleburg, VA
9.9 228 reviews

Middleburg Carriage House

farm, Middleburg
This charming farm stay is situated just 2 kilometres from the historic centre of Middleburg, offering easy access to the town's shops and restaurants, while also being close to local wineries and polo fields. The property has received excellent ratings for its cleanliness, location, and overall experience.
The accommodation has two bedrooms and one bathroom, comfortably sleeping up to four guests. The property offers modern amenities, including a fully equipped kitchen, air conditioning, and a spacious outdoor area with a flagstone patio, perfect for enjoying the scenic views of the vineyard and Blue Ridge Mountains.
Yellowwood Cottage - Private Outdoor Space Sophisticated  Sunny Luxurious Indoor - Middleburg, VA
10 109 reviews

Yellowwood Cottage - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

apartment, Middleburg
This detached house is located 800 metres east of Middleburg village, set within three acres of woodland, a short drive from Middleburg Historic District and Aldie Mill Historic Park.
This family-friendly property offers 260 square metres of living space for up to eight guests, featuring four bedrooms, three bathrooms, a modern kitchen with a dishwasher, air conditioning, a terrace, garden, spa, and parking.
Peaceful, Authentic Stone Cottage With Cozy Charm - Middleburg, VA
9.9 86 reviews

Peaceful, Authentic Stone Cottage With Cozy Charm

apartment, Middleburg
This smoke-free cottage is located in a peaceful rural area just 5 kilometres from Middleburg's main attractions, including the National Sporting Library & Museum, Tudor Day Spa, and The Sporting Gallery. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
This charming 3-bedroom, 2-bathroom property spans 139 square metres and comfortably sleeps up to 6 guests. The cottage offers a fully equipped kitchen, a private garden with barbecue facilities, and a terrace where you can relax and enjoy the fresh air.
Private Middleburg Estate - Middleburg, VA
No reviews

Private Middleburg Estate

gîte, Middleburg
This renovated 1890 colonial fieldstone manor house, offering a gîte experience, is situated on a 40-hectare estate less than 1 kilometre from Main Street Middleburg and the Salamander Resort & Spa, boasting historic features and rural vistas.
This family-friendly holiday home accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring air conditioning, Wi-Fi, a fully equipped kitchen, a garden, a swimming pool, and on-site adventure activities including zip lines and ATV rentals.

Best Middleburg, VA lodgings with a pool

Among the 2 accommodations in Middleburg, VA, here are the 2 best ones with a pool

2 Minutes To The Upperville Horse Show - Middleburg, VA
10 1 review

2 Minutes To The Upperville Horse Show

apartment, Middleburg
This six-bedroom, six-bathroom house is located in Upperville, Virginia, an 11-minute (approximately 18 km) drive from Middleburg's Historic District and a 16-minute (approximately 26 km) drive from Sky Meadows State Park.
The 392-square-metre property offers a private pool, garden, and parking, accommodating up to 16 guests and including amenities such as a fully equipped kitchen, Wi-Fi, and air conditioning.
Historic Middleburg Equestrian Estate - Middleburg, VA
9.9 50 reviews

Historic Middleburg Equestrian Estate

apartment, Middleburg
This historic equestrian estate is located in Mountville, just under 16 km from Middleburg's town centre and close to the Salamander Resort and Spa and the Goodstone Inn. The property has consistently received excellent user ratings for its location, cleanliness and overall experience.
This 5-bedroom, 5-bathroom house can accommodate up to 10 guests. The property offers a range of amenities including a swimming pool, a garden, a fitness centre and a fully equipped kitchen, as well as high-speed internet access and a range of outdoor activities including hiking trails and cycling routes.

Frequently asked questions about accommodations in Middleburg, VA

  • What are the must-see sites in or near Middleburg, VA?

    Middleburg is known for its beautiful countryside and equestrian heritage. You must visit the National Sporting Library & Museum, a treasure trove of sporting history. The charming downtown area is also worth exploring, with its historic buildings and quaint shops. For a scenic escape, head to the nearby Sky Meadows State Park, offering hiking trails and stunning views.
  • What are the best accommodations in Middleburg, VA?

    Among the accommodations in Middleburg, VA, Private Carriage House, "When Pigs Fly" Airbnb Most Hospitable Host In Va and The Red Fox Inn & Tavern are the most popular ones.

  • How can travelers reach Middleburg, VA?

    The closest airport to Middleburg is Washington Dulles International Airport (IAD), about a 50-minute drive away. You can also reach Middleburg by car, taking Interstate 66 East to Route 50 West. If you're travelling from Washington D.C., it's a scenic 1-hour drive.
  • What are the best accommodations with a pool in Middleburg, VA?

    Tyrolean Garden Suite With Privat Ent In Art Villa, The Hunt Box @ Tally Yo Farm and Inn At Evergreen are the best accommodations with a pool in Middleburg, VA.

  • When is the ideal time to plan a trip to Middleburg, VA?

    The best time to visit Middleburg is during the spring or autumn, when the weather is mild and the foliage is at its peak. The International Gold Cup, held in October, is a popular event that draws crowds to Middleburg. The summer months can be hot and humid, while winter can be chilly and snowy.
  • What are the best accommodations with a jacuzzi in Middleburg, VA?

    The best accommodations with a jacuzzi in Middleburg, VA are Tyrolean Garden Suite With Privat Ent In Art Villa, Villa Maud and Goodstone Inn & Restaurant.

  • What are the best walking or cycling routes in Middleburg, VA?

    Middleburg itself is a charming town to explore on foot, with its historic buildings and quaint shops. For a longer walk or bike ride, head to the scenic trails at Sky Meadows State Park, offering breathtaking views of the Blue Ridge Mountains. The 10-mile loop around the town, starting at the Middleburg Town Hall, is a popular choice for cyclists.
  • What are the best accommodations for families and kids in Middleburg, VA?

  • What nearby towns or cities can be explored from Middleburg, VA?

    Middleburg is conveniently located within a short drive of several interesting towns and cities. You can explore the historic city of Alexandria, visit the bustling city of Washington D.C., or enjoy the charming atmosphere of Leesburg, known for its wineries and breweries. For a taste of rural Virginia, head to the quaint town of Upperville, known for its equestrian heritage.
  • What are the best pet friendly accommodations in Middleburg, VA?

  • What amenities can travelers expect from accommodations in Middleburg, VA?

    Middleburg offers a range of accommodation options, from charming bed and breakfasts and historic inns to luxury hotels and country estates. Many accommodations feature amenities like swimming pools, tennis courts, and spa services. You can also find restaurants, cafes, and bars within walking distance of most hotels.
  • What are the best accommodations with parking in Middleburg, VA?

    Private Carriage House, "When Pigs Fly" Airbnb Most Hospitable Host In Va and The Red Fox Inn & Tavern are the best accommodations with parking in Middleburg, VA.

Popular destinations

Best Middleburg, VA accommodations with a garden

Middleburg Carriage House Studio - The Loft - Middleburg, VA
10 26 reviews

Middleburg Carriage House Studio - The Loft

apartment, Middleburg
This studio apartment is located near Middleburg, Virginia, offering convenient access to the historic village, Salamander Resort, and major routes to Washington D.C. and Dulles Airport.
The property features a fully equipped kitchen, queen-sized bed, private washer/dryer, and a fenced-in backyard with garden seating, with electric vehicle charging and secure parking also available.
Grand 9br Manor Ideal For Weddings & Gatherings - Middleburg, VA
10 7 reviews

Grand 9br Manor Ideal For Weddings & Gatherings

apartment, Middleburg
Provenance Manor, a nine-bedroom Georgian estate near Middleburg, Virginia, sits on 121 private acres, offering seclusion yet proximity to the historic district and local wineries.
This spacious property, sleeping up to 16 guests, boasts a chef's kitchen, a game room with ping-pong and shuffleboard, extensive lawns, and a fire pit, alongside five and a half bathrooms and ample indoor and outdoor seating areas.
Middleburg Carriage House Flat Coachmans Quarters - Middleburg, VA
10 85 reviews

Middleburg Carriage House Flat Coachmans Quarters

apartment, Middleburg
This newly renovated Middleburg apartment, situated in a 1930s Carriage House near the village centre, offers easy access to shops, restaurants, and the Salamander Resort, and is less than 80km from Washington, D.C., and Dulles Airport.
The two-bedroom, one-bathroom flat sleeps three, features a private garden with firepit, secure parking, EV charging, and a sunroom with a Charleston twin bed, alongside full-size kitchen appliances and a smart lock.
Guest House On Horse Farm -2 Bedrooms/2 Bath - Middleburg, VA
10 35 reviews

Guest House On Horse Farm -2 Bedrooms/2 Bath

apartment, The Plains
This tranquil A-frame guest house, situated in The Plains, Virginia, within the renowned Horse Country, offers easy access to local equestrian attractions and wineries.
The self-catering property sleeps up to six guests in two bedrooms and two bathrooms, featuring a fully equipped kitchen with appliances including a dishwasher and a fieldstone shower, plus a cosy living room with a fireplace; a larger three-bedroom house is also available to rent.

Best Middleburg, VA accommodations with a kitchen

Fox Hill Farm Retreat - Middleburg, VA
10 26 reviews

Fox Hill Farm Retreat

house, Middleburg
This eight-acre Middleburg estate, a two-minute drive from the town centre and adjacent to Greenhill Winery, offers stunning countryside views and is close to historic Middleburg, Virginia.
The 6,500+ sq ft property boasts four bedrooms, four bathrooms, and sleeps twelve, featuring a fully equipped kitchen, fitness centre, ample parking, and is available for private events.
Country Bank Barn - Middleburg, VA
9.9 284 reviews

Country Bank Barn

farm, Middleburg
This charming farm stay is situated in a peaceful neighbourhood in Middleburg, just a short distance from fine dining, numerous wineries, and outdoor activities. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers four bedrooms and three bathrooms, comfortably accommodating up to six guests. Guests can enjoy a recently renovated deck and patio, perfect for relaxing and enjoying the tranquil surroundings.
Welcome To Virginias Horse & Wine Counry - Middleburg, VA
No reviews

Welcome To Virginias Horse & Wine Counry

apartment, Purcellville
This newly completed, bright, and spacious one-bedroom flat is situated on a secluded 25-acre farm in the Middleburg/Philomont area, offering a peaceful retreat near local equestrian activities.
This accommodation comfortably sleeps up to four guests with a queen bed and queen pullout sofa, featuring a fully equipped open-plan kitchen, high-speed internet, in-unit laundry, a 65-inch smart TV, and an optional horse boarding facility.
Luxury Villa W/ Private Pool & Game Lounge - Middleburg, VA
No reviews

Luxury Villa W/ Private Pool & Game Lounge

house, Bull Run Mountain Estates
This luxury villa in Bull Run Mountain Estates is situated 35 kilometres from Washington D.C. and close to Loudoun's wineries.
Boasting 465 square metres of living space, this 3-bedroom, 3-bathroom accommodation comfortably hosts up to 10 guests, featuring a private swimming pool and an entertainment lounge.
©2026 cozycozy.com