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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 7 Villas in Upperville with updated reviews, rates, and availability.

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)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
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, (21)
"Thank you for making our stay so seamless. We were comfortable and able to have a lot of fun and get a lot accomplished. It’s a great area!"
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 | 6BR | 6.5BA | 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!
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

18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (35)
"We absolutely loved this little cottage. It's a great location near Middleburg, tucked back in the woods. It's got everything you need for a peaceful retreat. A perfect place to curl up in front of the fire with a book. The host was so welcoming and easy to work with. We'll definitely be back!"
The price is AED 1,010
AED 1,446 total
includes taxes & fees
26 Jan - 27 Jan
18th Century Stone Cottage minutes from historic Middleburg
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, (244)
"Our group had an amazing stay at the Bear Chase Manor! The house has great common space areas and the pool was a huge hit with everyone. We also loved the convenience of being next to the brewery along with the incredible views of nature. Can't wait to have the opportunity to stay here again!"
Breathtaking views with an indoor private pool, come escape with us
Charles Town Home w/ Private Pool & Hot Tub
Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub
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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