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Compare 255 Vacation Homes in Middleburg with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"
Trailside Retreat in breathtaking Western Loudoun

1805 Farmhouse with Heated Pool in Harpers Ferry

10.0 out of 10, Exceptional, (37)
"The house and property were absolutely perfect for our group. Lots of privacy, the renovations are very well done. All technology is top of the line and works as expected. The pool, or in our case hot tub, was even better than we expected. It was used both nights we were there. The barn apartment is a wonderful place for some additional privacy from a large group, and is extremely comfortable. We would recommend this house 100%. "
1805 Farmhouse with Heated Pool in Harpers Ferry

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (47)
"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!"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Historic Hideaway

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at Janelle’s cottage in Leesburg. Every possible detail and amenity has been well thought out and provided. Janelle is an amazing host and very responsive. The fenced in back yard was great for our little fur baby. The beds were cozy and comfortable. The water pressure in the shower was wonderful. This is our new home away from home when we visit our daughter in Ashburn."
The price is SAR 563
SAR 1,191 total
includes taxes & fees
19 Mar - 20 Mar
Historic Hideaway

Modern Home on Middleburg Equestrian Farm

10.0 out of 10, Exceptional, (11)
"We had a lovely girls weekend away in this modern home tucked away in Middleburg. It was conveniently located near town and among rolling roads of horse country. The house was cosy, comfortable and had all the amenities of home. We especially liked the comf beds and Nespresso machine. "
Modern Home on Middleburg Equestrian Farm

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (9)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is SAR 525
SAR 1,325 total
includes taxes & fees
13 Mar - 14 Mar
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

10.0 out of 10, Exceptional, (6)
"Stayed with my three daughters for a Galentine’s weekend and had a great time! Enjoyed some of the nearby hiking trails and soaked up the quiet beauty of the area."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (95)
"Spacious, lovely, home that was perfect for 50th bday celebration with 8 women!"
Gruner Bungalow at Otium Cellars

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

10.0 out of 10, Exceptional, (54)
"The property is quite lovely, surrounded by the rolling hills of western Virginia. The house was perfect, a lot of space to spread out if needed. We spent our evenings on the screened in back porch. The pool and gardens were an added bonus. Every evening the neighbor cows would graze along the fence line- just a lovely get away from the City! "
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

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

9.8 out of 10, Exceptional, (27)
"Fantastic weekend with my family...highly recommend 3 Penny Acres!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (10)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area

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

9.8 out of 10, Exceptional, (246)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
Breathtaking views with an indoor private pool, come escape with us

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

9.6 out of 10, Exceptional, (17)
"We had a fantastic stay at the property. The home is very charming and the pool is great. The location was also really nice. Close to wineries and hiking. Two points of feedback are that the dishes were visibly dirty upon arrival and all of the mattresses need to be replaced. Everyone in the group slept poorly and noted that the mattresses were uncomfortable. The master bedroom should likely also have a larger bed."
The price is SAR 1,324
SAR 4,318 total
includes taxes & fees
6 Apr - 7 Apr
Buckskin Manor - Historic, Pool, 66 Acre Vineyard

New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After

9.8 out of 10, Exceptional, (12)
"Everything was perfect. The place was clean, it was a nice neighborhood with no noise. And the host was great at laying everything out and communicating during the process. It felt very safe and comforting. Overall it’s definitely a 5/5 stars from me!"
New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After

Spacious estate in charming Purcellville with WiFi, fitness room, AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful countryside, great selection of local wineries and accessible to West Virginia, this property is hard to beat."
Spacious estate in charming Purcellville with WiFi, fitness room, AC

Luxury Home. Hot-tub, close to IAD & Hylton PAC.

Luxury Home. Hot-tub, close to IAD & Hylton PAC.

The Lodge at Stoneleigh

10.0 out of 10, Exceptional, (7)
"Great house; perfect for family with lots of activities in the area as well."
The Lodge at Stoneleigh

JCS Farms | 4 Bed, 3 Bath

9.8 out of 10, Exceptional, (10)
"We had an incredible stay at JCS Farms.Beautiful, clean house. Lots of space. The main floor open concept was awesome for our family gathering/celebration. It was an extremely peaceful setting. Star gazing, nature, birds, and the sunrise every morning through the kitchen doors and bedroom windows! Just a fantastic stay and will definitely stay again. Joshua was so kind and helpful! "
JCS Farms | 4 Bed, 3 Bath
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, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is SAR 1,032
SAR 1,489 total
includes taxes & fees
20 Mar - 21 Mar
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, (126)
"Excellent modern layout. Close proximity to Dulles Airport. Will be looking forward to another stay!"
The price is SAR 513
SAR 1,004 total
includes taxes & fees
16 Mar - 17 Mar
Global Luxury Suites at Reston Town Center

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

9.8 out of 10, Exceptional, (246)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
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.