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

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
Pet-Friendly Berryville Home: Walk to Main Street!
9.4 out of 10, Exceptional, (11)
"Sparking clean. Comfortable and has everything anyone would want for a relaxing stay in Berryville. "
Pet-Friendly Berryville Home: Walk to Main Street!
NEW LISTING! Mountain Chic Retreat by RedAwning
2.0 star property
10.0 out of 10, Exceptional, (1)
"I grew up in Jeff Co, but never explored this area of the county. Great house very peaceful! Only feedback and down side was NO laundry machines on site. "
The price is AED 560
AED 1,674 total
includes taxes & fees
16 Nov - 17 Nov
NEW LISTING! Mountain Chic Retreat by RedAwning
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
Big Sunny Family House
10.0 out of 10, Exceptional, (22)
"This was a girls’ trip for a homesteaders conference. We enjoyed the spacious living spaces; the pictures just don’t give them justice. We had meals around the large dining table, then moved into the large living room for further conversation and fellowship. The bedrooms were great also. The neighborhood hosts several restaurants and coffee shops. Just a great experience! "
Big Sunny Family House
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
9.0 out of 10, Wonderful, (4)
"A wonderful cabin with great views of the farm. We loved seeing the cows and goats and the occasional visit from the peacock. The hosts are Amazing."
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
Mountain Getaway - 7 beds (2 King) - Large Common Area
10.0 out of 10, Exceptional, (9)
"Great place to stay for a family wedding. House was exactly how it was in the photographs. "
Mountain Getaway - 7 beds (2 King) - Large Common Area
Charles Town Townhome: 9 Mi to Harpers Ferry
10.0 out of 10, Exceptional, (8)
"I spent a week in the property and thoroughly enjoyed my stay. The check-in process was very smooth and the home is immediately welcoming. The downstairs is modern and spacious. It is a very family friendly place that is equally suited for single or couple travelers. I love the intentionality of blending a play nook for kids into a gathering area for adults. The upstairs is very comfortable. The master bedroom features a king beg that seemingly hugs you while you sleep. The en suite bath...
Charles Town Townhome: 9 Mi to Harpers Ferry
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!
Modern Country House on the Shenandoah River
9.8 out of 10, Exceptional, (29)
"Birds chirping, nice breezes and stunning views! Adventures down to the river and room for us all in the great room! Would love to go back!"
Modern Country House on the Shenandoah River
Hot Tub, Poker Table, River Access & Kayaks and Wineries
9.4 out of 10, Exceptional, (16)
" Worked for what we needed."
The price is AED 573
AED 1,526 total
includes taxes & fees
12 Nov - 13 Nov
Hot Tub, Poker Table, River Access & Kayaks and Wineries
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
10.0 out of 10, Exceptional, (91)
"We rented both of Missy‘s properties and went back-and-forth between them. She was super helpful and accommodating, and the properties were fantastic. Can’t say enough! "
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
9.8 out of 10, Exceptional, (50)
"Perfect house for my family. Perfect location for my granddaughter’s wedding. Only 1.2 miles The house was so well equipped with everything anyone would want or need. Loved the yard and all the surroundings. "
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (34)
"This house is located near wonderful walking paths and a short drive to Leesburg. It worked well for our group of 6 adults. We appreciated the fact that our bedrooms had access to individual bathrooms, each with lots of towels. Additionally, there is plenty of parking. "
Trailside Retreat in breathtaking Western Loudoun
Relax by the lake, wineries, hiking, history, casino fun just 16-min drive away
10.0 out of 10, Exceptional, (7)
"We had a wonderful time at the house! Took advantage of the hot tub and bon fire pit. It was an amazing way to end the days. The fenced in yard was amazing for our doggies and they loved the property as well. :) The third bed (downstairs) is more of a loft bed, so keep that in mind. My friend is very tiny so it wasn't an issue for her, but my mom wouldn't have been able to get into the space. FANTASTIC SPOT! "
Relax by the lake, wineries, hiking, history, casino fun just 16-min drive away
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (29)
"Beautiful cozy home with a fantast view. Fenced in deck (our dog loved it as well as the fenced in yard)! Great location for day hikes! "
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Sunny Front Royal Vacation Rental w/ Hot Tub!
9.8 out of 10, Exceptional, (7)
"A great property, beautifully decorated and furnished, located in a bucolic setting with a magnificent view of the mountains and skyline. Can't say enough how nice!"
Sunny Front Royal Vacation Rental w/ Hot Tub!
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 562
AED 1,121 total
includes taxes & fees
14 Nov - 15 Nov
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
Indigo Blue modern open vibe on tree lined street
10.0 out of 10, Exceptional, (3)
"The house was super charming and had lots of cool old-timey features that made it feel like stepping back in time. The neighborhood itself added to the old-town vibe. It was a huge house, perfect for a big family. "
Indigo Blue modern open vibe on tree lined street
Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown
2.0 star property
10.0 out of 10, Exceptional, (2)
"The house was nice & clean & the host was great to work with. We really enjoyed the stay & you must try the restaurant next door. It is delish. Hope to stay again."
Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown
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
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.8 out of 10, Exceptional, (45)
"Awesome place to stay lots to do"
The price is AED 742
AED 1,393 total
includes taxes & fees
19 Nov - 20 Nov
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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
9 Dec - 10 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.