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Holiday Homes in Middleburg

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Featured Holiday Homes in Middleburg

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
10.0 out of 10, Exceptional, (48)
"This property was perfect for our family reunion, in conjunction with a wedding in Middleburg. The house was interestingly rambling, and had perfect spaces for everyone who came. The grounds, garden, and swimming pool were cherries on top! It was the perfect setting for a large gathering, with plenty of spaces for different activities and conversations. Such a unique property!"
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Hot Tub, Poker Table, River Access & Kayaks and Wineries
9.8 out of 10, Exceptional, (7)
"Everything was fine."
The price is AU$655
includes taxes & fees
2 July - 3 July
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Historic gem in the heart of downtown Hamilton! Trees and a private stream
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Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
Breathtaking views with an indoor private pool, come escape with us
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (8)
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Historic and Updated Farmhouse Built in 1808
10.0 out of 10, Exceptional, (114)
"We had a great stay! Thank you!"
Historic and Updated Farmhouse Built in 1808
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (13)
"We were in town for the comedy show at the casino. House was within walking distance however not a walk you would want to take wearing heels. Very quiet neighborhood with plenty of restaurants close by. The house was very clean and comfortable beds. Had a really great time!! Thank you!!!"
The price is AU$440
includes taxes & fees
10 July - 11 July
Cozy home near Casino, Breweries, Historical attractions, National Park & more
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
Single family 4 bed home luxurious design in 1 acre lot
9.2 out of 10, Wonderful, (7)
"I booked this property for a group to stay for an equestrian event at Frying Pan Park. The house was perfect for our group. ITs well laid out, close to tons of restaurants, and to the venue. We had a blast and I would absolutely stay here again!"
Single family 4 bed home luxurious design in 1 acre lot
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (22)
"We had such a lovely time in Virginia. This property was so clean and well appointed. We also enjoyed the location right next to the W&OD trail."
Trailside Retreat in breathtaking Western Loudoun
Morrisonville Manor w/ Fire Pit & Hot Tub!
10.0 out of 10, Exceptional, (27)
"There were 9 adults and 1 baby in our group and the property worked out great for us. The owners had great communication and everything about the home came as advertised. Plenty of room, very clean, and some nice extra touches. We recommend and would stay here again."
Morrisonville Manor w/ Fire Pit & Hot Tub!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (21)
"We were a group of 10 people with 2 infants and absolutely enjoyed our stay. The location is amazing, nestled in the woods with deers and birds visiting the property. The house had everything we needed from linens to towels to utensils and toiletries. The listing says 4 bedrooms, but the bunk bed area in the basement can also be considered an additonal room. Would definitely recommend this place when visiting Virginia/Shenandoah NP."
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
10.0 out of 10, Exceptional, (14)
"We enjoyed the location of this quiet highland home away. It was close enough to amenities and sites, but far enough to feel like we were staying in the country. We were able to do day trips to Harpers Ferry, Winchester, Leesburg, Middleburg, but also just enjoyed this surroundings at the property. There were plenty of bed options and the kitchen was well-maintained and equipped. We will return."
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
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
Quick Drive to Everything in Charles Town
10.0 out of 10, Exceptional, (3)
"The house was perfect… close to everything, very clean. Plenty of space and a great Kitchen. With family near by this house made it very easy for us to visit and enjoy our time with them over Easter. We will be staying here again."
Quick Drive to Everything in Charles Town
Historic District,Entire upstairs
8.4 out of 10, Very good, (23)
"The property was nice. Unfortunately the house next door caught on fire while we were staying at this property. The house next door was a total loss. Very frightening!"
The price is AU$641
includes taxes & fees
12 July - 13 July
Historic District,Entire upstairs
Blue A Frame Minutes From Mountain Lake Club
10.0 out of 10, Exceptional, (10)
"We were traveling to the area for an AKC event, and stayed for three nights prior to Thanksgiving. Matt's house was the perfect home base location! Loved the moutain setting while still being convenient to the places we need to travel to. House was beautiful and clean, and we loved watching the deer roam the property. Second time staying at one of Matt's properties, and neither disappointed!"
Blue A Frame Minutes From Mountain Lake Club
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 AU$3,846
includes taxes & fees
7 July - 8 July
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
10.0 out of 10, Exceptional, (5)
"We were a group of 11 friends staying at the house for the Wine Country 10K. The house was amazing. The listing doesn’t even do it justice. Even though it rained on the main day we were there we were still able to hang out in the hot tub and around the bar, because they were covered, and enjoy meals together in the beautiful and well stocked kitchen and dining room. Despite being 11 adults in the house we didn’t feel at all cramped. There was a small issue in the morning while we were there, but...
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
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!
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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

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (17)
"Middleburg is a quaint Virginia town with lots of history, and to stay in this 1800 century cottage added to the entire experience. Tim (owner) is absolutely fabulous and so accommodating. Tim spent time with us (by our request) and gave us the history of the cottage and plantation. The cottage is well stocked, comfortable, and exactly as the pictures show. But to sit out on the patio looking out over the landscape was wonderful and so peaceful! Middleburg, itself, is full of wineries, shops and...
The price is AU$594
includes taxes & fees
14 July - 15 July
18th Century Stone Cottage minutes from historic Middleburg
Hyatt House Herndon/Reston
3.0 star property
9.0 out of 10, Wonderful, (1145)
"Beautiful area"
The price is AU$223
includes taxes & fees
16 June - 17 June
Hyatt House Herndon/Reston
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
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.

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