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Search Villas in Winchester

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Compare 69 Villas in Winchester with updated reviews, rates, and availability.

Pool
The most luxurious and sought-after Short-Term Rental in Wine Country.
10.0 out of 10, Exceptional, (10)
"Villa Fabulosa did not disappoint! Description and photos are completely accurate. There is nothing Alex missed with this property, and his communication leading up to and during our visit was appreciated. We found the QR codes throughout the villa to be extremely useful. The outdoor kitchen and game room were special treats too. Will definitely be planning another stay. Truly a stunning villa!"
The price is SAR 6,725
SAR 11,894 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The most luxurious and sought-after Short-Term Rental in Wine Country.
Exterior
Elsinore Lake Estate
3.0 star property
9.4 out of 10, Exceptional, (3)
"The house was great, nice and clean. We had a great stay and would like to come back. "
Elsinore Lake Estate
Exterior
Temecula Vineyard View Mansion-AMAZING VIEWS, Pool/Hot Tub, 10 Acres, Mini Golf
Temecula Vineyard View Mansion-AMAZING VIEWS, Pool/Hot Tub, 10 Acres, Mini Golf
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Enjoy a glass of wine on the balcony while watching the gorgeous sunset.
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
9.8 out of 10, Exceptional, (26)
"Loved the property we stayed at. Avantstay manages the property and was available for any issues we had 24/7. Only issue was on our end working the app for pool/spa operation, lol."
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
Property grounds
Resort Style Ranch/infinity pool for family
9.4 out of 10, Exceptional, (13)
"Very grateful to have found this place for my birthday trip! It's rare to find a place that sleeps so many people comfortably and doesn't just jam a bunch of bunk beds into every room to maximize on the amount of beds. We all enjoyed the kitchen especially and I appreciated how the hot tub was timed to turn on and off so that we didn't have to think about it. The couches were stained with dirt, but I attribute that to previous guests who have no regard for cleanliness and ignore the hosts'...
The price is SAR 2,363
SAR 5,056 total
includes taxes & fees
25 Jum. II - 26 Jum. II
Resort Style Ranch/infinity pool for family
Exterior
Villa 5B/3B with pool/spa/mini golf putting
9.8 out of 10, Exceptional, (13)
"My friends and I had a blast staying at this beautiful home. It is close to many wineries, and has views of wine country from the property. We felt safe and secure with the coded gate to enter the property. The inside of the house was spacious and felt very fancy. The pool, hot tub, and outdoor area were awesome too! It was a great space to relax with friends, with close proximity to wine tasting during the day. I would definitely recommend!"
The price is SAR 1,496
SAR 3,962 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Villa 5B/3B with pool/spa/mini golf putting
Welcome to La Barrique!
La Barrique by AvantStay | Secluded 14 Acre Estate w/ Vball & Pool
9.6 out of 10, Exceptional, (29)
"Great location, especially for our venue. Everything was clean and nice. Would have liked a few things stocked. Overall, we enjoyed the stay."
La Barrique by AvantStay | Secluded 14 Acre Estate w/ Vball & Pool
Exterior
Villa with indoor pool in Temecula wine country-VRBO
9.2 out of 10, Wonderful, (14)
"We were there for my grandson's soccer tournament. This home was perfect, comfortable, and fully equipped to make you feel at home. only 10 minutes away from the soccer fields, the stores. Will certainly book again!!"
The price is SAR 1,872
SAR 4,439 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Villa with indoor pool in Temecula wine country-VRBO
Huge, landscaped backyard with a pool, hot tub, and plenty of space to lounge in the shade.
Burgundy by AvantStay | Basketball Crt, Pool, Hot Tub, Outdoor Kitchen!
10.0 out of 10, Exceptional, (11)
"This home was so charming. While the outside was a cottage from a fairy tale, the inside was filled with all the modern amenities needed for today. The beds and linens were so comfortable and provided the comfort for a great nights sleep! We brought our kids and close family friends to get away for my son’s 16th birthday. We enjoyed the spa, game room, and really enjoyed cooking in the well stocked kitchen. Our youngest thoroughly enjoyed the basketball court! I literally could not say enough...
Burgundy by AvantStay | Basketball Crt, Pool, Hot Tub, Outdoor Kitchen!
Le Grand Bleu by AvantStay | Luxury Hilltop Estate
9.8 out of 10, Exceptional, (89)
"Gorgeous views with lots of room and beautiful pool. Communication was prompt. Even better in person."
Le Grand Bleu by AvantStay | Luxury Hilltop Estate
Welcome Home!
Casa del Arbol by AvantStay | Stunning California Estate with Incredible Views
9.4 out of 10, Exceptional, (10)
"Beautiful property with amazing views! Sleeps only 8 adults comfortably. Hosts were extremely responsive. Overall great stay!"
Casa del Arbol by AvantStay | Stunning California Estate with Incredible Views
Pool
Villa Artemis - Luxurious Villa located in Temecula's Wine Valley
10.0 out of 10, Exceptional, (8)
"We LOVED our stay at this resort-like villa. It felt upscale but also cozy. Felt fully stocked and functioned well. The sound system and backyard felt like treats, the neighborhood was peaceful, comfortable and convenient. Wineries and downtown were easy to get to, however it is note-worthy that the last .3 miles of road to get to the house is unpaved, and was a little rough I'm sure because of the recent rains, but our SUVs handled it fine. Overall such a relaxing stay, would 100% return next...
Villa Artemis - Luxurious Villa located in Temecula's Wine Valley
Welcome to Palazzo Del Sol!
Palazzo Del Sol By AvantStay | Breathtaking Home w/ Mountain Views & Hot Tub
9.8 out of 10, Exceptional, (13)
"The home is beautiful! It's centrally located to all the wineries and restaurants. The home has amazing views and tons of room inside and out to enjoy. If you're looking for a large home to share with family and friends rent this home to make great memories!!"
Palazzo Del Sol By AvantStay | Breathtaking Home w/ Mountain Views & Hot Tub
Temecula is calling!
Bear Bridge by AvantStay | Hilltop Haven in Temecula w/ Views!
10.0 out of 10, Exceptional, (16)
"We thoroughly enjoyed the house! We had 6 adults and the house was spacious with great seating indoors and outdoors. Very nice furnishings. We enjoyed the views and the fire pit as well as the barbecue grill. The only concern we had was the room with the bunk beds is not suitable for 2 adults as the top bunk was inaccessible with the type of ladder for an adult to climb. Would recommend possibly replacing with 2 twin beds. There was also a comment that beds were a bit soft in other bedrooms....
Bear Bridge by AvantStay | Hilltop Haven in Temecula w/ Views!
The most breathtaking lake and mountain view
10.0 out of 10, Exceptional, (23)
"A real treat to stay here. Had a fantastic view and at nigh the bullfrogs and ducks made a great soundscape."
The price is SAR 1,309
SAR 2,323 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The most breathtaking lake and mountain view
Chateau Vino - French Style Chalet
10.0 out of 10, Exceptional, (29)
"We had a large group gathering here to celebrate my husband’s birthday. The house was perfect and the communication and property management was incredible. We were thankful for such a great place to spend time together!"
Chateau Vino - French Style Chalet
The Iron Mansion 🔥 9 Acre Luxurious Private Resort🏝️12000 ft Event Space!
10.0 out of 10, Exceptional, (23)
"The pictures did not do it justice. Normally I am impressed with pictures which usually sell the booking, then I get and say "eh, I guess it will work." Not the Iron Mansion! Impressed and then some. Cant wait to go back."
The price is SAR 4,287
SAR 7,952 total
includes taxes & fees
26 Jum. II - 27 Jum. II
The Iron Mansion 🔥 9 Acre Luxurious Private Resort🏝️12000 ft Event Space!
Panoramic
Hacienda-In center of Temecula Wine Country
10.0 out of 10, Exceptional, (15)
"We had a wonderful time during our stay as our daughter was married in Temecula. Michael was a wonderful host: super responsive, professional and generous. He went out of his way to help and accommodate and would highly recommend staying here."
The price is SAR 2,622
SAR 5,205 total
includes taxes & fees
30 Jum. I - 31 Jum. I
Hacienda-In center of Temecula Wine Country
Welcome to Via del Sur!
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
9.8 out of 10, Exceptional, (31)
"Great location and property. Plenty of room for everyone, especially larger groups"
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
Welcome to Owl's Nest! Amazing pool views overlooking 60 acre wine vineyards!
Owl's Nest by AvantStay | Infinity Pool w/ Incredible Views
9.8 out of 10, Exceptional, (37)
"Great house in a perfect spot. We had a corporate and the house was ideal."
Owl's Nest by AvantStay | Infinity Pool w/ Incredible Views
Don't see what you're looking for?
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

Chateau Vino - French Style Chalet
10.0 out of 10, Exceptional, (29)
"We had a large group gathering here to celebrate my husband’s birthday. The house was perfect and the communication and property management was incredible. We were thankful for such a great place to spend time together!"
Chateau Vino - French Style Chalet
View from property
Wine Country Oasis Retreat - Close to wineries
10.0 out of 10, Exceptional, (33)
"My family (6 adults) stayed at this property for a long weekend and thoroughly enjoyed ourselves. They checked in to make sure we got in okay and if we had any problems which we did not, but I like the responsiveness. It was very clean, relaxing and we all said that next year if we still have 6 we would like to stay here again."
Wine Country Oasis Retreat - Close to wineries
Exterior
The Cottages at Golden Village Palms
3.0 star property
9.6 out of 10, Exceptional, (28)
"Quaint, clean cottages. Comfortable bed. Had everything we needed for a night’s rest."
The price is SAR 566
SAR 632 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Cottages at Golden Village Palms
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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