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Middleburg, VA accommodations
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12 Lodgings in Middleburg, VA

Traveler-Approved Family-Friendly Accommodations in Middleburg, VA

Family vacations in Middleburg, VA work best when your lodging offers ample space and puts city attractions within easy reach.

Gorgeous, Wooded 3 Acre Estate -5 Bed/4  Bath-leesburg/brambleton/aldie Area - Middleburg, VA
9.8 145 reviews
Middleburg, VA
10/02 – 10/07
$919/nighttotal: $4595 (5 )

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-leesburg/brambleton/aldie Area

5 6
apartment , Brambleton
This family-friendly vacation home is located just 3 miles from Fleetwood Farm Winery and Evergreen Mills Equestrian and Hiking Trail, offering a peaceful escape in a rural setting near Leesburg. The home consistently receives excellent ratings for location, cleanliness, and overall user experience.
This 5-bedroom rental comfortably sleeps 10 guests. Enjoy modern amenities like a fully equipped kitchen, free WiFi, and a relaxing spa tub. The spacious home also features a patio, a garden, and a barbecue grill for outdoor enjoyment.
Historic Spacious Home In The Heart Of Upperville, Va - Middleburg, VA
10 6 reviews
Middleburg, VA
10/02 – 10/07
$866/nighttotal: $4330 (5 )

Historic Spacious Home In The Heart Of Upperville, Va

4 6
apartment , Middleburg
This Upperville vacation home, located 0.4 miles from Upperville Park and 6 miles from both Sky Meadows State Park and Paris Barns, offers easy access to local attractions and wineries.
This 4-bedroom, 4-bathroom house sleeps 10 guests comfortably, boasting a fully equipped kitchen, Smart TV, fireplace, barbecue grills, and a smoke-free environment.
Salamander Resort And Spa - Middleburg, VA
Middleburg, VA
10/02 – 10/07
$3068/nighttotal: $15340 (5 )

Salamander Resort And Spa

3 6
resort , Middleburg
Salamander Resort And Spa is located in Middleburg, Virginia, a short distance from the town center and within walking distance of the National Sporting Library and Museum, The Byrne Gallery, and Trowbridge-Lewis Galleries. This resort offers a variety of amenities, including a spa with massage rooms, sauna, and steam room, a fitness center, an outdoor pool, an indoor pool, a library, and a game room, making it a perfect destination for families and couples alike.
Gate House Cottage - Middleburg, VA
9.9 119 reviews
Middleburg, VA
10/04 – 10/15
$868/nighttotal: $9548 (11 )

Gate House Cottage

1 2
apartment , Middleburg
The Gate House is a charming cottage located just a short distance from Middleburg's vibrant downtown, offering easy access to shops, restaurants, and wineries. This historic property, part of a larger estate dating back to 1768, boasts excellent user, location, and cleanliness ratings.
The cottage features a cozy den, breakfast area, porch, and a bedroom with a built-in queen-sized bed and a marble bathroom. Guests can enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, parking, and Wi-Fi, as well as activities like walking, cycling, and exploring the surrounding countryside.

Best Middleburg, VA lodging with a pool

Among the 4 accommodations in Middleburg, VA, here are the 4 best ones with a pool

2 Minutes To The Upperville Horse Show - Middleburg, VA
Middleburg, VA
10/02 – 10/07
$1753/nighttotal: $8765 (5 )

2 Minutes To The Upperville Horse Show

6 6
apartment , Middleburg
This six-bedroom, six-and-a-half-bathroom house in Upperville is an 11-minute drive from Middleburg's Historic District and a 16-minute drive from Sky Meadows State Park.
The 4,220-square-foot home comfortably sleeps 16 guests and features a private pool, garden, fully equipped kitchen, and laundry facilities, plus Wi-Fi.
Historic Middleburg Equestrian Estate - Middleburg, VA
10 45 reviews
Middleburg, VA
10/04 – 10/15
$2340/nighttotal: $25740 (11 )

Historic Middleburg Equestrian Estate

5 2
apartment , Middleburg
This equestrian estate is located just outside of Middleburg, Virginia, less than 10 minutes from Goodstone Inn, the Salamander Resort and Spa, and charming downtown Middleburg. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The main house features a large, modern, and open kitchen, a formal dining room, a formal living room, a spacious theater room, and a large wine cellar, offering ample space for up to 10 guests. Enjoy a stunning pool, cabana, outdoor kitchen, expansive gardens, hiking trails, multiple outdoor dining areas, a working horse farm, and high-speed Starlink internet.
Historic Aldie Farmhouse Near Middleburg And Wine Country - Middleburg, VA
9.6 28 reviews
Middleburg, VA
10/04 – 10/15
$383/nighttotal: $4213 (11 )

Historic Aldie Farmhouse Near Middleburg And Wine Country

4 2
farm , Bull Run Mountain Estates
This family-friendly vacation rental near Aldie, Virginia, is conveniently located within six miles of Aldie Mill Historic Park, Bull Run Country Club, and Quattro Goomba's Winery.
This four-bedroom, three-bathroom farmhouse sleeps eight guests and boasts a swimming pool, terrace, game room, barbecue grills, and free internet access.
Private Middleburg Farm - Middleburg, VA
Middleburg, VA
10/02 – 10/07
$4681/nighttotal: $23405 (5 )

Private Middleburg Farm

1 6
gîte , Middleburg
The Foxstone Estate Farm, a historic 1890 colonial fieldstone manor home near Middleburg, offers a unique rural escape on nearly 100 acres, situated less than 5,280 feet from Main Street Middleburg and Salamander Resort & Spa. This family-friendly vacation rental accommodates up to 10 guests with four bedrooms and three bathrooms, featuring air conditioning, internet, a full kitchen with a dishwasher, and access to a swimming pool, garden, and parking, alongside unique farm life encounters and outdoor activities.

Frequently Asked Questions about accommodations in Middleburg, VA

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

    You can't miss the National Sporting Library & Museum, which celebrates equestrian history, and the beautiful architecture of the historic downtown area, including the Middleburg Town Hall. Just outside town, you'll find the impressive Oatlands Plantation, a preserved 18th-century estate.
  • 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 easiest way to get to Middleburg is by car. It's about an hour's drive from Washington, D.C., and about 90 minutes from Baltimore. You can also take the train to the nearby town of Manassas and then take a taxi or rent a car.
  • 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.

  • What outdoor activities can visitors enjoy in and around Middleburg, VA?

    Middleburg is a great place for hiking and biking. The scenic trails at the nearby Sky Meadows State Park are popular with locals, and you can also enjoy horseback riding at one of the many equestrian farms in the area. If you're looking for something a little more relaxed, you can always take a stroll through the beautiful gardens at Oatlands Plantation.
  • What are the best accommodations with a jacuzzi in Middleburg, VA?

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

    Spring and fall are the most popular times to visit Middleburg, as the weather is mild and the foliage is beautiful. If you're a fan of equestrian events, you'll want to plan your trip around the International Gold Cup, held in October. The town is also lovely during the summer, but it can get hot and humid.
  • What are the best accommodations for families and kids in Middleburg, VA?

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

    For walking, the downtown area is very walkable, and you can enjoy a leisurely stroll through the historic streets. For cycling, the scenic route along the Old Dominion Trail is popular, offering a 45-mile stretch from Purcellville to Bluemont. It's a great way to see the countryside.
  • What are the best pet friendly accommodations in Middleburg, VA?

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

    You can easily make a day trip to the charming town of Leesburg, which is just a short drive from Middleburg. Leesburg has a lively downtown area with lots of shops and restaurants, and it's also home to the impressive Morven Park, a historic estate with a museum and gardens. If you're looking for a bigger city, Washington, D.C. is about an hour's drive away.
  • 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.

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

    Middleburg offers a range of accommodations, from cozy bed and breakfasts to luxurious hotels. Many accommodations offer amenities like swimming pools, fitness centers, and restaurants. You can find options that cater to different budgets and preferences.

Destinations nearby

Best Middleburg, VA accommodation with a garden

Middleburg Carriage House Flat Coachman’s Quarters - Middleburg, VA
10 74 reviews
Middleburg, VA
07/03 – 07/06
$476/nighttotal: $1428 (3 )

Middleburg Carriage House Flat Coachman’s Quarters

1 2
apartment , Middleburg
This newly renovated Middleburg, Virginia apartment, located minutes from the historic village center and Salamander Resort, offers easy access to wineries, breweries, and walking trails.
The two-bedroom, one-bathroom rental sleeps three guests and features a full kitchen, private entrance with smart lock, secure parking with EV charging, a fenced yard with firepit, and scenic views.
Chandelier Farmhouse In Historic Bluemont Virginia - Middleburg, VA
9.6 8 reviews
Middleburg, VA
10/02 – 10/07
$1062/nighttotal: $5310 (5 )

Chandelier Farmhouse In Historic Bluemont Virginia

5 6
apartment , Round Hill
This historic 5-bedroom manor house estate in Round Hill, Loudoun County, offers a unique lodging experience with proximity to Bluemont Vineyard, Great Country Farms, and the Appalachian Trail, all within a scenic countryside setting.
This expansive property, ideal for large gatherings, features two living areas, a well-equipped kitchen, a wrap-around porch with scenic views, an outdoor campfire area, and guest concierge services for customized experiences.
Middleburg Carriage House - Middleburg, VA
9.9 223 reviews
Middleburg, VA
07/03 – 07/06
$597/nighttotal: $1791 (3 )

Middleburg Carriage House

1 2
farm , Middleburg
This farm is located just a two-minute drive from Middleburg's historic downtown, nestled in the countryside amidst vineyards and polo fields. It boasts excellent user, location, and cleanliness ratings, making it a highly recommended choice for travelers. The carriage house offers a unique and charming stay with a capacity for four guests. Amenities include a fully equipped kitchen, air conditioning, a spacious patio, and a beautiful garden, perfect for enjoying the peaceful country setting and exploring nearby attractions.
Charming Cottage On Horse Farm Middleburg Area - Middleburg, VA
10 121 reviews
Middleburg, VA
10/04 – 10/15
$263/nighttotal: $2893 (11 )

Charming Cottage On Horse Farm Middleburg Area

1 2
gîte , Bull Run Mountain Estates
This charming cottage is located in Aldie, Virginia, just 5 minutes from historic Middleburg and a short drive from Bull Run Mountain Estates, offering a peaceful escape in hunt country. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom cottage comfortably accommodates two guests. Enjoy amenities like a fully stocked kitchen, a private garden, and pet-friendly accommodations, along with the option to explore the surrounding horse property and nearby attractions.

Best Middleburg, VA accommodation with a kitchen

The Black Aframe - Hot Tub And Mountain Views - Middleburg, VA
Middleburg, VA
10/02 – 10/07
$449/nighttotal: $2245 (5 )

The Black Aframe - Hot Tub And Mountain Views

2 6
house , Bull Run Mountain Estates
This Bull Run Mountain Estates house, located in Evergreen Farms, is 16 miles from the Dulles Expo Conference Center and 12 miles from Washington Dulles International Airport.
This 1290 sq ft vacation home accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, complimentary WiFi, air conditioning, a hot tub, and mountain views.
6 Mi To Historic Leesburg: Apt W/ On-site Dining - Middleburg, VA
Middleburg, VA
10/04 – 10/15
$213/nighttotal: $2343 (11 )

6 Mi To Historic Leesburg: Apt W/ On-site Dining

1 2
apartment , Hamilton
This Hamilton apartment is located steps from Catoctin Valley and 1.3 miles from The Barns at Hamilton Station Vineyards.
This non-smoking rental offers complimentary self-parking, free WiFi in public areas, and an equipped kitchen with a microwave oven, air conditioning, and a television.
Vista At Highfields Farm - Middleburg, VA
Middleburg, VA
10/02 – 10/07
$2006/nighttotal: $10030 (5 )

Vista At Highfields Farm

1 6
gîte , Middleburg
This modern 3-bedroom gîte is situated on 3 acres in Middleburg, just a short drive from the historic downtown area and local attractions. The gîte offers a tranquil retreat with ample space for relaxation and enjoyment, and can accommodate up to 6 guests.
Guests can enjoy a fully equipped kitchen with Miele appliances, a Samsung washer and dryer, and a smart home system with speakers and Apple TVs. The spacious backyard features a fire pit that can comfortably accommodate 16 guests, perfect for evening gatherings. Guests may also have the opportunity to participate in activities at the neighboring farm, including horseback riding and polo lessons.
"Secretaria" - Tranquil 1 Br Apt - Middleburg, VA
10 11 reviews
Middleburg, VA
07/03 – 07/06
$352/nighttotal: $1056 (3 )

"Secretaria" - Tranquil 1 Br Apt

1 2
apartment , Middleburg
This ground-floor Middleburg, VA apartment, located 3 miles southwest of town, offers a peaceful rural retreat near Middleburg's shops and wineries.
The one-bedroom, one-bathroom unit sleeps two, features a recently updated kitchen and bathroom, a dedicated workspace, and access to fresh eggs from heritage breed chickens; guests can also enjoy observing India blue peacocks and Sebastapol geese on the property.
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