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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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, (42)
"Very friendly host. Very spacious, quiet place. Perfect for our family for my son's wedding in Fallbrook. "
Chateau Vino - French Style Chalet
Priv. Resort! Mountain Views Oasis- Heated Pool & Spa, Game Rm, Temecula-8 miles
Outdoor pool, a heated pool

Priv. Resort! Mountain Views Oasis- Heated Pool & Spa, Game Rm, 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
20 May - 21 May
Priv. Resort! Mountain Views Oasis- Heated Pool & Spa, Game Rm, 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

9.2 out of 10, Wonderful, (30)
"We had such a fun time! The property was perfect!"
The price is AED 1,612
AED 4,067 total
includes taxes & fees
14 May - 15 May
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, (7)
"We came from nearby for a quick staycation, Meiko House fit our needs perfectly. Plenty of bedrooms with comfortable beds and bathroom space was plentiful. Yard and pool area well maintained. Recommend!"
The price is AED 661
AED 1,690 total
includes taxes & fees
20 May - 21 May
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
22 May - 23 May
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, (20)
"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 1,466
AED 3,880 total
includes taxes & fees
18 May - 19 May
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)
"Beautiful property and wonderful experience. We had a group of 18 people stay here for the weekend, and everyone had a great time!! We will be back for sure. "
The price is AED 2,913
AED 7,352 total
includes taxes & fees
9 Jun - 10 Jun
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, (11)
"Great location and place"
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)
"Property was absolutely phenomenal. We've stayed at a lot of VRBO's & these photos were spot on with the property! Well done to the Hosts for all the help."
The price is AED 8,789
AED 14,643 total
includes taxes & fees
29 May - 30 May
Voted Vacation Rental of The Year out of millions of homes on VRBO!
The most breathtaking lake and mountain view
Outdoor dining

The most breathtaking lake and mountain view

9.8 out of 10, Exceptional, (30)
"A real treat to stay here. Had a fantastic view and at nigh the bullfrogs and ducks made a great soundscape."
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)
"Spacious, quiet, lots of amenities "
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)
"5-Stars! Wonderful! The house had a true luxury feel—well maintained, very clean, and stocked with great amenities. The kitchen had everything we needed, the beds were incredibly comfortable with extra linens, and the layout was perfect for a large group. Its proximity to wineries and nearby activities made it even better. We’d love to return!"
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, (93)
"Great for families who like options for privacy, but still enjoy the fun of gathering at the pool and living spaces! Beds were comfortable and plenty of everything in the kitchen!"
Le Grand Bleu by AvantStay | Luxury Hilltop Estate
Hacienda-In center of Temecula Wine Country
Bathtub, jetted tub, hair dryer, towels

Hacienda-In center of Temecula Wine Country

9.8 out of 10, Exceptional, (20)
"Everything as advertised. Owner extremely helpful. Great location for family gathering. Highly recommend!"
The price is AED 1,649
AED 3,937 total
includes taxes & fees
14 May - 15 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)
"They space was very accommodating for our our group and we loved how quiet and restful it was. "
Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
Outdoor dining

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

9.8 out of 10, Exceptional, (37)
"Wonderful place and location. Perfect for a large group. "
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!
Casa Verde - Villa with private pool, spa, game room & home theater
Outdoor dining

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, (32)
"The home is spacious, beautiful, and conveniently located near wineries. Gorgeous views. Kitchen well appointed. Hosts were in good communication. Highly recommend!"
The price is AED 1,726
AED 4,209 total
includes taxes & fees
18 May - 19 May
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

1 Bed Room Casita-Suite with Private Entrance
Outdoor pool

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (40)
"Very nice neighborhood and close to shopping. Host is very communicative."
The price is AED 213
AED 510 total
includes taxes & fees
18 May - 19 May
1 Bed Room Casita-Suite with Private Entrance
Chateau Vino - French Style Chalet
Exterior

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (42)
"Very friendly host. Very spacious, quiet place. Perfect for our family for my son's wedding in Fallbrook. "
Chateau Vino - French Style Chalet
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)
"8 cousins and our spouses (50-70 years old)were able to Spend 6 nights reminiscing our childhood memories and making more special memories. Our host, Sam was awesome and very personable to work with from the first day I booked! I recommend anywhere in the area to check it out!!"
The price is AED 3,599
AED 6,691 total
includes taxes & fees
14 May - 15 May
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
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.

Frequently asked questions

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