Photo by Stephanie Sutton

Holiday Homes in Middleburg

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Featured Holiday Homes in Middleburg

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (242)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us

Cozy guest room with WiFi and AC in charming Sterling

The price is AU$194
includes taxes & fees
30 Dec - 31 Dec
Cozy guest room with WiFi and AC in charming Sterling

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
Terra Alta - Incredible River Views and Hot Tub!

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

10.0 out of 10, Exceptional, (62)
"We were looking for the perfect place to stay during our week in hunt country- convenient to the farm where we kept our horses and the restaurants in Middleburg. This exceeded our expectations. This house has been lovingly restored and is beautifully decorated. Its cozy, traditional vibe meshes perfectly with its modern updates. There are thoughtful touches everywhere- from a large selection of coffees, to the working fireplace, and many more. The beds and bedding are super comfortable. We...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (95)
"The home was in excellent condition, clean, beautiful and overall lovely. Close to Middleburg, a delightful small town. We felt like we were in the country, but close to everything we wanted to do."
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Cozy Entire Guest Suite by IAD Intl. Airport

5.2 out of 10, (5)
"Close to Dulles Airport, although it is a small space it had everything I needed. Water pressure is good in the shower, toilet takes a while to fill and is crammed in a corner. "
The price is AU$258
includes taxes & fees
30 Dec - 31 Dec
Cozy Entire Guest Suite by IAD Intl. Airport

The PINK PEARL in Historic Leesburg

9.6 out of 10, Exceptional, (31)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg

Stunning House! Minutes From Shenandoah River

10.0 out of 10, Exceptional, (19)
"Lovely and well maintained home in a quiet neighborhood!"
Stunning House! Minutes From Shenandoah River

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (7)
"Highly recommend this place."
Cozy Country Getaway in the Heart of Upperville

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

9.6 out of 10, Exceptional, (13)
"We had a small family gathering here around Christmas and we absolutely loved it! We immediately felt right at home. It is a gorgeous property, well appointed, and very comfortable. The game room was a huge hit with everyone. We're hoping to make it an annual tradition, hopefully for longer than one night next time!"
The price is AU$995
includes taxes & fees
6 Jan - 7 Jan 2025
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Romantic Stone Cottage Circa 1869-75 acres to Hike

9.2 out of 10, Wonderful, (5)
"Unfortunately we happened to stay when there was a wind storm in the county so we lost power, water and heat for the night. We texted the host to check on candles and/or flashlights but were told to “just use our phones”. (Not really an option when you’ve been traveling all day and phones are almost dead). The cottage is very rustic and not quite as comfortable as the pictures make it out to be. The bed is extremely firm so be aware if you have bad hips or back. There’s also glade plug ins in...
Romantic Stone Cottage Circa 1869-75 acres to Hike

Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA

Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
The price is AU$849
includes taxes & fees
30 Dec - 31 Dec
Quaint Royal Cottage @ Historic Leesburg

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (25)
"Hiking, playing in the creek, S'mores by the fire pit, enjoying meals on the porch all add up to fun memories. We enjoyed our stay. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (92)
"Wonderful Thanksgiving in a wonderful home with our family."
Gruner Bungalow at Otium Cellars

A private 2BR & living area w/ patio for 4

9.0 out of 10, Wonderful, (6)
"Place was clean and comfortable. It was a very nice neighborhood!"
The price is AU$526
includes taxes & fees
14 Jan - 15 Jan 2025
A private 2BR & living area w/ patio for 4

River Front Retreat

8.8 out of 10, Excellent, (35)
"The home is in a very cool location. We loved the drive to the house. There were great views of the river. The home had everything needed to enjoy the river, but our stay was too cold to enjoy the river. Overall, the home was just what we were looking for!"
River Front Retreat

Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

10.0 out of 10, Exceptional, (11)
"We hosted Thanksgiving weekend at the house and it perfectly accommodated our large group as well as the varying ages (31-89). House is well organized and amenities were all as described. Plenty of dishwater and glasses for a large group although if you are hosting a large meal bring some disposable platters and a cocktail shaker. Few minutes drive to Purcellville which had plenty of options for live sports and other dinners. Beautifully decorated with plenty of space. Also nice to be at the...
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

10.0 out of 10, Exceptional, (45)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (34)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AU$640
includes taxes & fees
30 Dec - 31 Dec
18th Century Stone Cottage minutes from historic Middleburg

Global Luxury Suites at Reston Town Center

3.5 star property
8.2 out of 10, Very good, (121)
"The location, the building and the property manager, Bushra, were excellent. Lots of local businesses are walkable and a great Reston Town Center location. "
The price is AU$463
includes taxes & fees
2 Jan - 3 Jan 2025
Global Luxury Suites at Reston Town Center

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (242)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.