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Compare 9 Villas in Upperville with updated reviews, rates, and availability.

Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…
Living area
Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…
10.0 out of 10, Exceptional, (2)
"Our family of five needed a house near my aging / sick folks and this house was perfect! The owner was very hands on from a communication perspective and my kids loved all the amenities!"
Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…
Stunning Former Winery w/ Pool & Mtn Views!
Berryville Vacation Rental | 8BR | 5.5BA | Stairs Required | 7,078 Sq Ft
Stunning Former Winery w/ Pool & Mtn Views!
9.4 out of 10, Exceptional, (9)
"Everything was what we hoped for. Very nice place. Only negative was the lack of weeding. Thank you!"
Stunning Former Winery w/ Pool & Mtn Views!
Private10000sf Retreat GuitarPool Hottub-Wine Area
Private10000sf Retreat GuitarPool Hottub-Wine Area
10.0 out of 10, Exceptional, (19)
"Things were crazy due to a storm that came through right before we arrived but all ended up well and the kids had a blast. Paul always available if/when we needed him"
The price is SAR 6,000
SAR 9,874 total
includes taxes & fees
24 Sep - 25 Sep
Private10000sf Retreat GuitarPool Hottub-Wine Area
Historic Virginia Wine Country Villa w/ Pool, Yard
Hume Vacation Rental Villa | 6 Bedrooms | 6 Full Bathrooms | 2 Half Bathrooms
Historic Virginia Wine Country Villa w/ Pool, Yard
7.6 out of 10, Good, (15)
"The rooms were very engaging. My daughter-in-law was charmed. We had lots of indoor places in which to play. The pool in the backyard was great for adults & children during the warm summer!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Elegant Paris Manor w/ Private Pool!
Paris Vacation Rental | 7BR | 7.5BA | 10,000 Sq Ft | Stairs Required
Elegant Paris Manor w/ Private Pool!
10.0 out of 10, Exceptional, (1)
"Wonderful property with wonderful people. The Manor house is incredible. The pool and the outdoor space was exactly what we had hoped for. Everyone really enjoyed the wagon ride to the top of the property. Definitely would recommend this family or just a getaway for 2 on a weekend!! John"
Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!
Exterior
Elegant Paris Manor w/ Private Pool!
3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
Pool
Historic Virginia Wine Country Villa w/ Pool, Yard
3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Stunning Former Winery w/ Pool & Mtn Views!
Exterior
Stunning Former Winery w/ Pool & Mtn Views!
3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
Expansive 6000 sq ft Villa w/ Hot Tub, Fire Pit & 15+ acres
Exterior
Expansive 6000 sq ft Villa w/ Hot Tub, Fire Pit & 15+ acres
2.0 star property
Expansive 6000 sq ft Villa w/ Hot Tub, Fire Pit & 15+ acres
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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.
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Other property types in Upperville

Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (235)
"We were so excited to see that the Bear Chase Manor was available for the weekend of my daughter’s wedding. We knew this house would allow our family to enjoy the beautiful views and build lifelong memories. It was the perfect house for our special weekend. I highly recommend this house! "
Breathtaking views with an indoor private pool, come escape with us
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Crimson Lane!
Exterior from the deck
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Crimson Lane!
10.0 out of 10, Exceptional, (67)
"We had an excellent 4-night stay at Rachelle and Don's cabin. They were good communicators and eager to please. The cabin was clean, cozy and comfortable with a modern vibe. We loved how quiet it was. The large elevated deck overlooking the woods was great for enjoying our morning coffee and having dinner and a drink. It's close to local hiking and not far from a nice small town and Shenandoah National Park, etc. We would definitely recommended this cabin (and we'll be back)."
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Crimson Lane!
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Dining
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (44)
"Beautiful cabin! We loved the steam shower and the cabin was very clean and organized with everything we needed. It was great to sit on the deck and watch all the deer roam the property. The cabin was a short drive to Harper’s Ferry where we spent time hiking and then returned to the cabin to relax by the fire pit. Communication with the owner was excellent. Highly recommend!"
The price is SAR 488
SAR 1,165 total
includes taxes & fees
21 Oct - 22 Oct
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.

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