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Compare 268 Vacation Homes in Middleburg with updated reviews, rates, and availability.

Property grounds
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
10.0 out of 10, Exceptional, (36)
"Our time spent at the Farm House was wonderful! 14 of us from 12-80 years old all had a bed and a place at the dining room table! Perfect setting inside and out to celebrate my husbands birthday with all our children and grandchildren! We will be returning for future celebrations!"
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
Smart TV, fireplace, table tennis, books
Hot Tub, Poker Table, River Access & Kayaks and Wineries
10.0 out of 10, Exceptional, (5)
"It was great. Nice property, awesome location. Very private"
The price is $152
$410 total
includes taxes & fees
May 22 - May 23
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Smart TV
Cozy Country Getaway in the Heart of Upperville
10.0 out of 10, Exceptional, (1)
"The house was as advertised and very clean. The house instructions were clear and check out instructions where minimal. We had some slight confusion on working the thermostat and the bedrooms became much warmer in the evening, than the main areas. But as long as you knew that you could turn the temperature way down. Overall, the house was very comfortable and was a great location for us to spend two evenings during our visit."
Cozy Country Getaway in the Heart of Upperville
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Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (12)
"The home is beautiful! The owners did an amazing job to make us feel welcomed and at home. They provided us we unexpected amenities like coffee creamer, bottle water and even a bottle of wine. We greatly appreciated the free Netflix especially since ti rained during part of our stay. The location is ideal for our weekend adventures."
The price is $135
$288 total
includes taxes & fees
May 22 - May 23
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Private kitchen | Paper towels
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
10.0 out of 10, Exceptional, (10)
"The three of us saw Anne Wilson, went to the Bible Museum, and went to Cornerstone Chapel in Leesburg. We enjoyed several Leesburg eateries: Buford Biscuits, Cowbell Kitchen, and Lightfoot, and Rebellion. We really wished we had more time in your beautiful home. It was so serene and peaceful to be out in the woods."
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Smart TV, fireplace
Bull Run Estate: Luxury Retreat w/ Scenic Views by RedAwning
10.0 out of 10, Exceptional, (1)
"Great for lots of family and friends so everyone is together and not hotel room or hotel lobby hopping"
Bull Run Estate: Luxury Retreat w/ Scenic Views by RedAwning
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Berryville Home: Walk to Main Street!
10.0 out of 10, Exceptional, (5)
"Great house, like brand new. Right around the corner from Main st which has nice coffee shops and a few eateries. Very nice place and location in Berryville for those visiting the valley or the mountains just across the Shenandoah River. Thanks"
Pet-Friendly Berryville Home: Walk to Main Street!
Fridge, microwave, stovetop, dishwasher
Townhome in Leesburg Historic District!
10.0 out of 10, Exceptional, (10)
"Stayed four nights while our house was listed for sale. Had everything we needed, clean and comfortable and a great location a stone’s throw from all the coffee shops, restaurants and boutiques of downtown Leesburg. Bonus was the flower and garden festival. Location was mostly quiet but some street noise during the day/evening only which is to be expected so not an issue at all. House is wonderfully historic with all modern amenities/new upgraded appliances!"
Townhome in Leesburg Historic District!
Outdoor dining
A unique mountaintop getaway overlooking Willow Croft Winery.
10.0 out of 10, Exceptional, (81)
"This is a lovely home in a beautiful location. The hosts were wonderful and friendly. We were attending a wedding at Stone Tower Winery and this is the prefect location - less than a mile from the winery (great for that late night drive home from the wedding)! The home is also very close to downtown Leesburg."
A unique mountaintop getaway overlooking Willow Croft Winery.
Fridge, microwave, oven, stovetop
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (20)
"My family and I decided to book this home for our Easter holiday. I am so glad that we did! We absolutely loved this home. The downstairs was perfect for our kids, just the best hangout area for them to relax and have their own space. The fenced in yard and gated deck was perfect for our pup too. It was just so picturesque, and we really enjoyed the neighbor's chickens and herd of deer that'd visit daily. The house is about a 20-minute drive to Front Royal which we went to for dinner and is...
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Property grounds
Historic and Updated Farmhouse Built in 1808
10.0 out of 10, Exceptional, (113)
"Every detail was very thoughtful. We spent our time on the beautiful patio by the fire. It was a great getaway for our whole family."
Historic and Updated Farmhouse Built in 1808
TV, fireplace, stereo
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
10.0 out of 10, Exceptional, (1)
"We stayed at Loving Gallery & Studio last weekend with a group of 15 for our Mothers 90th Birthday The home is just beautiful and well laid out for large groups. There are 6 beautiful bedrooms plus sofa beds and all the possible amenities! Lots of wood for stoves, fireplaces & firepit, bathroom amenities, bottled water in each room, well stocked kitchen with spices and everything you could possibly need for cooking in your home away from home. There are also several beautiful outdoor spaces to...
The price is $1,360
$1,953 total
includes taxes & fees
May 28 - May 29
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
Outdoor dining
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
10.0 out of 10, Exceptional, (4)
"The house was amazing! The hosts really went out of their way to be accommodating and have all the necessities big or small! You can explore the town or have a cozy night in!"
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
Outdoor spa tub
Harpers Ferry Home w/ Private Pool & Hot Tub!
10.0 out of 10, Exceptional, (2)
"We absolutely loved this house. The location was so perfect and overlooks the river. Can be enjoyed in all seasons but the pool will be amazing in the summer. We enjoyed the wineries but struggled to get Ubers around town. All of the wineries and breweries have beautiful views as well. Great for a friends weekend !"
Harpers Ferry Home w/ Private Pool & Hot Tub!
Exterior
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
10.0 out of 10, Exceptional, (49)
"My wife and I were looking for a quick weekend getaway and found this beautiful historic house and it was perfect! The home is charming, cozy and warm. It was super clean (and smelled amazing) with all the modern amenities you would want. The kitchen was fully stocked with everything you need to whip up a meal and the beds were super comfy when you ate too much of it. The backyard is completely fenced in, which was great with our little pups, and beautiful at night with the bistro lights hung...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
Fridge, microwave, oven, stovetop
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
10.0 out of 10, Exceptional, (82)
"My family stayed here during a weekend trip to Middleburg for a wedding. The house was clean, comfortable, and had everything we needed. The downstairs and outside areas were perfect for our young kids."
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Smart TV, table tennis, books, offices
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (83)
"This was a beautiful home for a 30 something Bachelorette Weekend. The proximity to the tasting room was convenient and the grounds were beautiful. Our groups had an excellent time and hope to be back!"
Gruner Bungalow at Otium Cellars
Property grounds
Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (44)
"Stayed here for work. Had 5 guys at the house. Plenty of room and great deck to hang out on."
Terra Alta - Incredible River Views and Hot Tub!
Fridge, microwave, oven, stovetop
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
Exterior
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
9.8 out of 10, Exceptional, (15)
"We had a great time at this adorable farmhouse! Our family of 5 enjoyed cooked meals together at the table, tea and coffee every morning, and board games every night! Tom was extremely hospitable and made sure our stay was perfect!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Don't see what you're looking for?
See all available properties in Middleburg
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.

Other property types in Middleburg

Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is $270
$391 total
includes taxes & fees
Jun 9 - Jun 10
18th Century Stone Cottage minutes from historic Middleburg
Fridge, microwave, oven, stovetop
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
Exterior
Hyatt House Herndon/Reston
3.0 star property
9.0 out of 10, Wonderful, (1141)
"Flew into Dulles and the hotel was about 15 minutes away. We went to Shenadoah National Park which was about 1.25 from the hotel. Clean and wifi was good."
The price is $132
$154 total
includes taxes & fees
Jun 1 - Jun 2
Hyatt House Herndon/Reston
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.

Middleburg Vacation Homes information

Number of reviews
704
Accommodation
268 Vacation Homes
Lowest Price
$135
Highest Price
$1,360

Recent reviews of Middleburg hotels
Expedia verified reviews