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Compare 8 Villas in Winchester with updated reviews, rates, and availability.

Private10000sf Retreat GuitarPool Hottub-Wine Area
10.0 out of 10, Exceptional, (16)
"We had a wonderful stay at this VRBO and Paul was great! Would 100% stay again!"
Private10000sf Retreat GuitarPool Hottub-Wine Area
The front entrances to Westcott House
Westcott House- Privacy, amenities and space all in one beautiful package!
9.8 out of 10, Exceptional, (81)
"If you're planning a getaway with a large group of friends and seeking a serene retreat in the heart of Virginia, look no further than this rental house in Luray. From the moment we arrived, we were greeted with warmth and comfort, setting the tone for an unforgettable stay."
Westcott House- Privacy, amenities and space all in one beautiful package!
Berryville Vacation Rental | 8BR | 5.5BA | Stairs Required | 7,078 Sq Ft
Stunning Former Winery w/ Pool & Mtn Views!
9.2 out of 10, Wonderful, (5)
"-Convenient market <1 mile away where we could pick up last-minute essentials (i.e. ibuprofen)."
Stunning Former Winery w/ Pool & Mtn Views!
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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
Paris Vacation Rental | 6BR | 6.5BA | 10,000 Sq Ft | Stairs Required
Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!
View from property
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
10.0 out of 10, Exceptional, (4)
"This place was like having a resort to ourselves. Very clean and accommodating. The home owner is very personable. From the beautiful quarry, to the swings, floating docks, white beaches and kerokee room this is a true paradise. Come to your next adventure here!"
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Exterior
Elegant Paris Manor w/ Private Pool!
3.0 star property
Elegant Paris Manor w/ Private Pool!
Pool
Historic Virginia Wine Country Villa w/ Pool, Yard
3.5 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Exterior
Stunning Former Winery w/ Pool & Mtn Views!
3.5 star property
Stunning Former Winery w/ Pool & Mtn Views!
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See all available properties in Winchester
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.

Other property types in Winchester

Exterior
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (143)
"We really enjoyed the secluded location. It felt just far enough away but also easy to get to the cities nearby. We had a few issues with bugs, but nothing unexpected for mountain life. The kitchen was well stocked and the wifi worked surprisingly well during our stay. This was great for our girls trip and we would definitely come here again!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Secluded Cabin with hot tub on back deck
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (244)
"We really enjoyed the property. It was clean. Internet worked well. Washer and dryer was nice. Too cold to enjoy the hot tub for me. My suggestions are a new shower head, thank goodness I didn’t have to wash my hair. The flow is too spread out and not enough to efficiently rinse as you shower. Second is a cheaper Kcup machine would be nice. Traveling with ground coffee is not really ideal for a quick trip away. Third thing I suggest is two beach towels (minimum) for the use of the hot tub. We...
The price is AED 367
AED 1,161 total
includes taxes & fees
29 May - 30 May
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (27)
"Nice room and outdoor space. Nearby highway noise detracted from outside atmosphere. Bed was very comfortable, pleasant accommodations . It would be nice to have a breakfast included as there are no nearby places to eat."
Family Farmhouse Inn
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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