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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 111 Villas in Winchester with updated reviews, rates, and availability.

Chateau Vino - French Style Chalet
Exterior

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (39)
"The property "
Chateau Vino - French Style Chalet
Resort Luxury Oasis- Mtn Views, heated pool and spa, game room, Temecula-8 miles
Outdoor pool, a heated pool

Resort Luxury Oasis- Mtn Views, heated pool and spa, game room, Temecula-8 miles

3.0 star property
10.0 out of 10, Exceptional, (3)
"This property has amazing views on the main floor and is very clean. The outdoor area is also very appointed and great for groups. Our party of 8 including 2 infants had a lot of fun. There are only two things that would make the stay better: a door in the primary bathroom would be nice for privacy and sound proofing. The other en suite downstairs is behind the garage and really feels like a maid’s room. "
The price is AED 2,530
AED 3,788 total
includes taxes & fees
29 Apr - 30 Apr
Resort Luxury Oasis- Mtn Views, heated pool and spa, game room, Temecula-8 miles
Villa with indoor pool in Temecula wine country-VRBO
Fridge, microwave, oven, stovetop

Villa with indoor pool in Temecula wine country-VRBO

9.4 out of 10, Exceptional, (26)
"Enjoyed the spaciousness of the property for our slumber party and Old Town weekend! Perfect for large family/friends to sit together at the table."
The price is AED 1,804
AED 4,255 total
includes taxes & fees
13 Apr - 14 Apr
Villa with indoor pool in Temecula wine country-VRBO
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,
A heated pool

Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,

2.0 star property
10.0 out of 10, Exceptional, (5)
"Everything was perfect, we had an amazing experience, highly recommended "
The price is AED 661
AED 1,690 total
includes taxes & fees
14 Apr - 15 Apr
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,
3-Acres Estate, 3000 sqft, near Winery in Fallbroo
Pool

3-Acres Estate, 3000 sqft, near Winery in Fallbroo

10.0 out of 10, Exceptional, (1)
"Had a great experience staying at this property. Huge land and space and very secluded from other neighbors. "
The price is AED 624
AED 1,690 total
includes taxes & fees
15 Apr - 16 Apr
3-Acres Estate, 3000 sqft, near Winery in Fallbroo
Villa 5B/3B with pool/spa/mini golf putting
Outdoor pool, a heated pool

Villa 5B/3B with pool/spa/mini golf putting

9.2 out of 10, Wonderful, (18)
"We were at group of about 11guests and the home felt spacious. Enjoyed the jacuzzi and the proximity to some of the best wineries! The management was prompt to reply to our messages. Wonderful stay… will definitely recommend to grit!"
The price is AED 1,660
AED 4,080 total
includes taxes & fees
13 Apr - 14 Apr
Villa 5B/3B with pool/spa/mini golf putting
Get One Night Free!!! See below for more info!
Outdoor pool, a heated pool

Get One Night Free!!! See below for more info!

10.0 out of 10, Exceptional, (129)
"The location of this house was perfect being central to most wineries (also walking distance to a few). We loved the common spaces, especially the open kitchen / living space. Definitely recommend for a large group, as the # of bedrooms and bathrooms were perfect!"
Get One Night Free!!! See below for more info!
Camila by AvantStay | 18-Person Temecula Mansion
Pool

Camila by AvantStay | 18-Person Temecula Mansion

9.8 out of 10, Exceptional, (8)
"Check in was easy! The home was exactly as described and just divine for a few days away with the girls!!"
Camila by AvantStay | 18-Person Temecula Mansion
Private 1-Bedroom Villa on 12 Acres in Temecula Wine Country
Exterior

Private 1-Bedroom Villa on 12 Acres in Temecula Wine Country

10.0 out of 10, Exceptional, (10)
"We had a lovely stay at this charming BnB in wine country. Everything was just right — clean, cozy rooms, a peaceful setting. Enjoyed sitting outside in the morning and evening enjoying the view. Perfect spot to unwind after a day of wine tasting. Highly recommend! "
Private 1-Bedroom Villa on 12 Acres in Temecula Wine Country
Voted Vacation Rental of The Year out of millions of homes on VRBO!
A heated pool

Voted Vacation Rental of The Year out of millions of homes on VRBO!

10.0 out of 10, Exceptional, (23)
"From the moment you arrive at Villa Fabulosa, you feel as if you've been transported to another country. It's Ibiza-inspired charm is felt around every corner, from the clean architectural lines to the stunning panoramic vistas of Temecula. The kitchen is the BEST stocked kitchen I've ever come across in a vacation home. Everything to feed a crowd is there and if you're a coffee lover, there is even a milk frother! The house operates like a smart house, but fear not, there are QR codes...
Voted Vacation Rental of The Year out of millions of homes on VRBO!
The most breathtaking lake and mountain view
Smart TV, fireplace, books

The most breathtaking lake and mountain view

9.8 out of 10, Exceptional, (29)
"It was a very relaxing stay. My friends and I booked a weekend for a birthday party. The host was very responsive and accommodating. The house was clean upon arrival and looked exactly like the pictures. The only thing is the drive to the house because of how windy the roads are but it was worth it. "
The most breathtaking lake and mountain view
Beautiful Villa located in Temecula Wine Country
Outdoor pool

Beautiful Villa located in Temecula Wine Country

9.2 out of 10, Wonderful, (19)
"Great location in wine country, great views, and spacious home. Host was accommodating and responsive throughout our stay. "
Beautiful Villa located in Temecula Wine Country
Grand Lux II - Luxury Resort Pool Villa - Close to Wineries, Beaches, Temecula
Outdoor pool

Grand Lux II - Luxury Resort Pool Villa - Close to Wineries, Beaches, Temecula

10.0 out of 10, Exceptional, (29)
"Stayed here for our wedding weekend and it just made the whole experience even better. Was able to host our wedding party and enjoy the space. House was clean and had everything we needed. Location was close to our venue. Thank you for the amazing hospitality! "
Grand Lux II - Luxury Resort Pool Villa - Close to Wineries, Beaches, Temecula
Le Grand Bleu by AvantStay | Luxury Hilltop Estate
Pool

Le Grand Bleu by AvantStay | Luxury Hilltop Estate

9.8 out of 10, Exceptional, (92)
"This property is 30 minutes to Cahuilla MX track and Fox Raceway which we enjoyed immensely. The hot tub is very large with strong jets to massage us after our days f riding mx bikes. The five bedrooms were large and comfortable. Kitchen is large and stocked with everything we needed. BBQ was fantastic! We will definitely be back. Only negative we experienced was the $100.00 per day charge for the hot tub propane which was unexpected. I would include this fee with the rental."
Le Grand Bleu by AvantStay | Luxury Hilltop Estate
Hacienda-In center of Temecula Wine Country
A heated pool

Hacienda-In center of Temecula Wine Country

10.0 out of 10, Exceptional, (18)
"We enjoyed our stay for a family getaway. The house is amazing and we really enjoyed the poolside bbq and patio. It’s a great place to spend time with a large family with plenty of room to spread out. "
The price is AED 1,833
AED 4,121 total
includes taxes & fees
6 May - 7 May
Hacienda-In center of Temecula Wine Country
Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views
Pool

Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views

9.0 out of 10, Wonderful, (7)
"Easy to check in, great communication with host. Lots of support with any questions. Booked for a work retreat and we had no issues. Everyone loved the stay! Would come back here!"
Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
Terrace/patio

Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!

9.8 out of 10, Exceptional, (37)
"We gathered to celebrate my mon’s 90th birthday. The home was perfect for our family. We all slept comfortably, had our meals together, played games and enjoyed each other’s company. The kitchen was big and open allowing us to gather and cook together. "
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
Casa Verde - Villa with private pool, spa, game room & home theater
Pool

Casa Verde - Villa with private pool, spa, game room & home theater

9.2 out of 10, Wonderful, (15)
"Great home for families - appreciate the single level and the sleeping rooms being at one end. We will definitely be back and share with others!"
Casa Verde - Villa with private pool, spa, game room & home theater
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
Pool

De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub

9.6 out of 10, Exceptional, (29)
"This was a great place for our family to meet, gather, eat, and enjoy the scenery. "
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
Resort Style Ranch/infinity pool for family
Outdoor pool, a heated pool

Resort Style Ranch/infinity pool for family

9.2 out of 10, Wonderful, (31)
"Overall, the property was exactly as pictured. It was completely stunning. My only complaint is that the outlets in the master bathroom did not work and we were using that bathroom to get ready for my wedding."
The price is AED 2,028
AED 4,535 total
includes taxes & fees
13 Apr - 14 Apr
Resort Style Ranch/infinity pool for family
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 Winchester

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Pool

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (19)
"Our family had an incredible stay at Daisy’s Resort & Retreat! The house was spacious enough for everyone to spread out and have their own space, which made our stay so much more enjoyable. The kitchen was well-stocked with everything we needed, making it easy to prepare meals and feel right at home.We spent time exploring Old Town Temecula, which was just a short drive away. The location is perfect – close to all the Temecula Wine Country wineries, Old Town, and Pechanga Resort Casino. Yet, the...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
Pool

Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

2.0 star property
9.0 out of 10, Wonderful, (4)
"Overall very clean, so much open space to do activities. Everyone was happy! They provided gifts for the guests and provided toiletries for everyone which was nice. If there were any issues, we’d call Sam and a representative would swing by the house to fix everything. So overall it was great for the entire group!"
The price is AED 3,599
AED 6,585 total
includes taxes & fees
14 Apr - 15 Apr
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
1/Bed Room Casita-Suite with Private Entrance
Outdoor pool

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (39)
"Perfect for a quick overnight stay. "
The price is AED 213
AED 491 total
includes taxes & fees
14 Apr - 15 Apr
1/Bed Room Casita-Suite with Private Entrance
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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