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Compare 201 Vacation Homes in Upperville with updated reviews, rates, and availability.

800' of Glorious Shenandoah River frontage + 18 Private Acres

10.0 out of 10, Exceptional, (6)
"This property was awesome! Clean, nicely furnished, extra supplies if needed and a great layout. Two firepits were such a bonus. One by the house and one by the river. We will be returning!"
800' of Glorious Shenandoah River frontage + 18 Private Acres

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (36)
"Beautiful home. Nice location Enjoyed our stay very much"
Trailside Retreat in breathtaking Western Loudoun

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (20)
"What a wonderful stay! This VRBO was perfectly clean and super homey. We loved the decor and welcoming touches. I stayed with my colleagues for a week of offsite meetings, so we appreciated the many bedrooms and bathrooms plus the open meeting space. The wifi was a bit slow at times for our purposes working remotely. I'm sure a more casual user wouldn't have any issues. The location was fantastic. So peaceful and secluded feeling, but in reality just a short drive to Purcellville and Leesburg....
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Hot Tub, Poker Table, River Access & Kayaks and Wineries

9.6 out of 10, Exceptional, (17)
"My extended family met in Harper’s Ferry for a hiking weekend, and this was a perfect home base! Enough room for 8 of us plus dogs, and a beautiful outdoor space. We will definitely be back!"
The price is AED 573
AED 1,526 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries

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

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

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, (87)
"This was our third time staying at this beautiful property for our strategic planning session, and once again, it was a fantastic experience. The house is always spotless, spacious, and beautifully decorated, making it feel like a true home away from home. The host provided delicious meals throughout our stay, which added an extra level of convenience and enjoyment. Each meal was thoughtfully prepared and absolutely delicious—perfect for keeping our team energized and focused. The peaceful...
Gruner Bungalow at Otium Cellars

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (44)
"Perfect. No complaints at all. Thank you again. "
The price is AED 635
AED 1,183 total
includes taxes & fees
17 Dec - 18 Dec
Cottage on King | Charming Historic Leesburg Home

Pet-Friendly Berryville Home: Walk to Main Street!

9.2 out of 10, Wonderful, (12)
"The house was lovely and we wanted for nothing. I only want to report that the sink in the bathroom did not drain very well. Other suggestions, the bath tub should have better anti- slip coverage or a different product. Please include instructions on how to regulate the heat / air conditioner. "
Pet-Friendly Berryville Home: Walk to Main Street!

Townhome in Leesburg Historic District!

10.0 out of 10, Exceptional, (18)
"Lovely property and well appointed. Close to bars and restaurants and lovely outside area"
Townhome in Leesburg Historic District!

Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

8.6 out of 10, Excellent, (4)
"Home differed slightly from photos rugs were not included and house paint colors are different than what's listed on VRBO. Great scenery and wildlife views. Some small issues with cleanliness in the bathroom upon arrival. Noisy neighborhood (dogs barking, lots of loud trucks and 4-wheelers tearing up the gravel road outside). Grooves in gravel road + driveway not easy for a small car or sedan to get through. I would recommend outdoor lighting by the porch entry. Was difficult to navigate walking...
The price is AED 511
AED 1,051 total
includes taxes & fees
3 Dec - 4 Dec
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (5)
"The cottage was just perfect for a short Girls Weekend trip. Jennifer and Federico were great communicators and responded quickly to any questions we had. The cottage is decorated nicely with lovely touches throughout. Comfortable beds. Loved the back yard. We sat in the Adirondacks most evenings and watched the deer graze! The location is wonderful for visiting Middleburg, Purcellville, Marshall and The Plains. Many wineries, breweries, shopping and good restaurants. And the mountain scenery...
Cozy Country Getaway in the Heart of Upperville

Indigo Blue modern open vibe on tree lined street

10.0 out of 10, Exceptional, (4)
"Great location, fenced in yard a real plus for our lab, comfy beds!"
Indigo Blue modern open vibe on tree lined street

Luxury Private Estate Mins to Winery /Brewery

3.5 star property
10.0 out of 10, Exceptional, (1)
"Property was perfect for six professional women to hold our retreat and get work done in a collaborative and comfortable environment!"
Luxury Private Estate Mins to Winery /Brewery

Historic home nestled in the heart of horse and wine country. Kids/pet friendly!

10.0 out of 10, Exceptional, (2)
"We had a wonderful weekend in Paris, VA and enjoyed the history of this beautiful old home. the hostess made sure we had everything we needed to accommodate having a toddler in our group. I would definitely stay here again!"
Historic home nestled in the heart of horse and wine country. Kids/pet friendly!

Warrenton Gem: Walk to Dtwn, Dogs Welcome

2.0 star property
10.0 out of 10, Exceptional, (1)
Warrenton Gem: Walk to Dtwn, Dogs Welcome

Charming Home with Yard Near Shenandoah River!

9.8 out of 10, Exceptional, (14)
"All was very, very good. "
Charming Home with Yard Near Shenandoah River!

Harpers Ferry Home w/ Private Pool & Hot Tub!

10.0 out of 10, Exceptional, (3)
"Great girls weekend spot. The view out back was beautiful, and the house was not far from the grocery store or restaurants. We enjoyed being at the house and did not feel the need to stay busy during our stay it was the relaxing weekend we needed. "
Harpers Ferry Home w/ Private Pool & Hot Tub!

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

10.0 out of 10, Exceptional, (61)
"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!

Bull Run Mountain Retreat

9.4 out of 10, Exceptional, (23)
"It was readily accessible to family in the area and those traveling to it. Game rooms were excellent for the children. Within easy distance to places in the area"
Bull Run Mountain Retreat
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 Upperville

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

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (15)
"Rustic."
The Oculus - Huge Cabin with a Hot Tub!

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (51)
"Comfy cabin with everything topline. Loved the sunroom and the steam shower. Daily watching deer feed and stroll through the yard below. Gus wasn’t happy about it but he still watched through floor to ceiling windows."
The price is AED 441
AED 1,107 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
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.