Middleburg holiday homes

We found 444 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:27 Nov - 4 Dec

Fully equipped kitchen
Rest & Relaxation & a glass of tea right here!
The White House
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
NZ$12,449
for 7 nights, 1 room
NZ$1,778 per night
includes taxes & fees
Hidden Hollow Farm - Pool; Game Rm; Sleeps 26, 45 min. to DC, Weddings/Corporate
15' tall Holiday tree will be up from Thanksgiving to late January.  It really is a sight to see!
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!
Newly replace 16' Windows give an expansive view of the house vineyard
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
Exceptional
(58 reviews)

Vinewood Estate Luxury Pool and Vineyard Retreat

Purcellville

8% off
NZ$18,096
for 7 nights, 1 chalet
NZ$2,585 per night
includes taxes & fees
Vinewood Estate Luxury Pool and Vineyard Retreat
Bedroom #1 with queen bed and full bathroom
Interior
Private kitchen
Exceptional
(22 reviews)

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

Bluemont

8% off
NZ$5,659
for 7 nights, 1 cabin
NZ$808 per night
includes taxes & fees
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
The Kitchen Nook offers additional seating, and a cozy place to read.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
Gather and enjoy meals in the spacious, fully stocked kitchen.
Extra-large mirror and vanity in the 'Purple Rain' room.
Exceptional
(6 reviews)

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

Waterford

8% off
NZ$6,282
for 7 nights, 1 room
NZ$897 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
Stairs to 2nd floor
Screened in porch with fans
Front entryway
Family room
Exceptional
(5 reviews)

New - The Farmhouse at 1702!

Delaplane

8% off
NZ$4,355
for 7 nights, 1 home
NZ$622 per night
includes taxes & fees
New - The Farmhouse at 1702!
Interior
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Front of cottage, French doors on left lead to stone patio
Living room/dining room from stairway landing.  French doors to stone patio.
Exceptional
(113 reviews)

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

Leesburg

15% off
NZ$5,117
for 7 nights, 1 home
NZ$731 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Living area
Terrace/patio
Dining
Interior
Exceptional
(45 reviews)

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

Bluemont

7% off
NZ$4,737
for 7 nights, 1 home
NZ$677 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Fully stocked kitchen
Open concept kitchen
Exterior
Outdoor dining
Exceptional
(5 reviews)

Sunset Lion Mountain Cabin near a Lake & Vineyards

Harpers Ferry

8% off
NZ$3,909
for 7 nights, 1 cabin
NZ$558 per night
includes taxes & fees
Sunset Lion Mountain Cabin near a Lake & Vineyards
Property grounds
Exterior
Interior
Interior
Exceptional
(18 reviews)

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

Front Royal

12% off
NZ$3,865
for 7 nights, 1 cabin
NZ$552 per night
includes taxes & fees
Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline
Exterior
Exterior
Private kitchen
Living area
Exceptional
(7 reviews)

Cozy A frame cabin in quaint Front Royal. Dog friendly

Front Royal

8% off
NZ$2,584
for 7 nights, 1 cabin
NZ$369 per night
includes taxes & fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
Exterior
Exterior
Dining
Interior
Exceptional
(73 reviews)

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

Leesburg

8% off
NZ$6,082
for 7 nights, 1 home
NZ$869 per night
includes taxes & fees
Storybook cottage on Leesburg's most historic block — walk to everything
Dining
Property grounds
Exterior
Property grounds
Exceptional
(27 reviews)

Apple Mountain Retreat

Linden

12% off
NZ$2,134
for 7 nights, 1 apartment
NZ$305 per night
includes taxes & fees
Apple Mountain Retreat
Living area
Outdoor spa tub
Living area
Interior
Exceptional
(61 reviews)

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Linden

8% off
NZ$5,795
for 7 nights, 1 home
NZ$828 per night
includes taxes & fees
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Kitchen with refrigerator, microwave, air fryer, toaster, & Keurig with pods
Brick patio with mid-1800s brick smokehouse that is on the property.
Primary queen bedroom
Primary bedroom with entrance to the kitchen on right and bathroom on left.
Exceptional
(76 reviews)

Historic 2-Bedroom in Old Town Warrenton, Virginia

Warrenton

8% off
NZ$2,163
for 7 nights, 1 apartment
NZ$309 per night
includes taxes & fees
Historic 2-Bedroom in Old Town Warrenton, Virginia
Interior
Property grounds
Interior
Property grounds
Exceptional
(26 reviews)

Historic Mountain Cottage at Blue Ridge Overlook

Bluemont

8% off
NZ$6,080
for 7 nights, 1 home
NZ$869 per night
includes taxes & fees
Historic Mountain Cottage at Blue Ridge Overlook
Private kitchen
Property grounds
Outdoor dining
My home from the road.
Exceptional
(13 reviews)

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

Bluemont

8% off
NZ$2,867
for 7 nights, 1 apartment
NZ$410 per night
includes taxes & fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • 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 most popular type of holiday home accommodation in Middleburg?
Houses are the most popular style of holiday home in Middleburg, according to our data. Even if you've got something a little different in mind, Bookabach has holiday homes in loads of sizes and shapes. Browse our options to find your perfect Middleburg pad.
How much does it cost to rent a holiday home in Middleburg?
The average price for a holiday home in Middleburg is determined by several factors, like property type, length of stay and season. Whether you're dreaming about a sprawling villa with room to move around or a cosy cottage ideal for just you and the kids, just enter your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Middleburg?
The average price for a holiday home near the beach in Middleburg depends on when you're visiting the area and the style and size of property you're looking for. You can easily find prices on Bookabach by entering your destination and travel dates. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.
Are there pet-friendly holiday homes in Middleburg?
You're in luck. There are. You'll find three holiday homes that allow pets in Middleburg on Bookabach. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly holiday homes to book a place where your puppy dog can be near his favourite humans.
What are popular home amenities in Middleburg?
A barbecue grill, a firepit and a garden top the list of most popular home amenities in Middleburg. Whether you plan to go as a party of one, with your spouse or a group of best friends, Bookabach will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday homes in Middleburg?
With two Middleburg holiday properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a special celebration, Bookabach will help you book the perfect space to fit the occasion.
Are there holiday homes in Middleburg that welcome kids?
Bring the entire family together for fun-filled adventures in Middleburg at one of our three family-friendly holiday properties. Lots of these stays come with amenities that are suitable for getaways with children, including full kitchens, bunk beds and entertainment units. Just check the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Middleburg?
There are lots of fabulous things to do and see with the family in Middleburg, such as:
  • National Sporting Library & Museum
  • Red Fox Fine Art
  • The Sporting Gallery
How can I find holiday homes with air conditioning in Middleburg?
Select your travel dates and then use our filters to view holiday homes with ac in Middleburg on Bookabach. With three air-conditioned properties to choose from here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday home in Middleburg?
The minimum age is normally 16, 18 or 21. It can vary from one property to another on Bookabach, so look at the rules of your chosen Middleburg stay before making a booking.
How long can I rent a holiday home in Middleburg for?
The amount of time you can stay in a Middleburg holiday home for depends on the property. Simply enter your preferred travel dates to see options offering longer term stays. They come with the things you need to make your extended getaway more comfortable and enjoyable, like air conditioning and kitchens. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can hang around longer for less.