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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 8 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!"
The price is AED 3,629
AED 7,644 total
includes taxes & fees
3 Mar - 4 Mar
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!
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!
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
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, (36)
"Adorable cottage. Well appointef"
The price is AED 1,010
AED 1,439 total
includes taxes & fees
24 Feb - 25 Feb
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, (245)
"We stayed for three nights over a long weekend, arriving on Friday night and leaving Monday morning. 8 adults and six kids between 5 and 12. Check-in was easy. Location right next to the brewery was great. House is very big and well laid out. It does indeed have great views. A couple of things held this back from being 5 stars. First, the DirecTV did not work at first, which was important to us because of the NFL playoffs. We are grateful to Ben, the property manager, who worked hard on a...
Breathtaking views with an indoor private pool, come escape with us
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
Exterior from the deck

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (79)
"My husband and I had a lovely stay in this cabin for Thanksgiving. We had everything we needed to cook our Thanksgiving meal, stay cozy, and enjoy the views around the cabin. Thank you!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
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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