Photo by Betsy Wood

Search Villas in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 92 Villas in Winchester with updated reviews, rates, and availability.

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (35)
"We booked Chateau Vino to celebrate my mom’s 90th birthday. We wanted a home that fit our whole family comfortably. The house is amazing and having space to relax, eat, and enjoy the outdoors with seating for all was perfect. We had a wonderful time and hope to return again. "
Chateau Vino - French Style Chalet

The Most Exquisite Vacation Rental in Wine Country

10.0 out of 10, Exceptional, (22)
"We absolutely loved our stay at this property! It was the perfect setting for our company retreat with 10 people, and even with a full group, it never felt crowded. Everyone had plenty of space to spread out and enjoy privacy when needed, while the shared spaces were ideal for connecting and unwinding together. The fun and relaxation we experienced around the retreat sessions made our stay even more special. We even had a few people learn pickleball while we were there, adding to the...
The price is AED 5,851
AED 10,768 total
includes taxes & fees
17 Feb - 18 Feb
The Most Exquisite Vacation Rental in Wine Country

Villa with indoor pool in Temecula wine country-VRBO

9.4 out of 10, Exceptional, (24)
"A beautiful piece of property with lots of space and entertainment opportunities. The house was very spacious with gorgeous views of the Valley. Woke up to two hot air balloons taking off, majestic. "
The price is AED 1,901
AED 4,430 total
includes taxes & fees
10 Feb - 11 Feb
Villa with indoor pool in Temecula wine country-VRBO

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

10.0 out of 10, Exceptional, (9)
"It was a beautiful villa in the country. Such a relaxing few days. The villa is super clean, well stocked, and decorated perfectly. We enjoyed the views of vineyards and quietneighborhood."
Private 1-Bedroom Villa on 12 Acres in Temecula Wine Country

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 1,675 total
includes taxes & fees
9 Feb - 10 Feb
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,

The Iron Mansion 9 Acre Luxurious Private Resort🏝️12000 ft Event Space!

10.0 out of 10, Exceptional, (27)
"Our group had a fantastic time staying here. We had a 20 year high school reunion and everybody enjoyed their time. The house and the pool were clean and it was great having the guest house too. Would definitely recommend, great for parties large family gatherings. "
The price is AED 2,160
AED 5,235 total
includes taxes & fees
11 Feb - 12 Feb
The Iron Mansion 9 Acre Luxurious Private Resort🏝️12000 ft Event Space!

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 price is AED 1,466
AED 2,630 total
includes taxes & fees
18 Feb - 19 Feb
The most breathtaking lake and mountain view

Resort Style Ranch/infinity pool for family

9.2 out of 10, Wonderful, (29)
"It was a wonderful cozy spot to enjoy family. We played games, played pool, and cooked and ate to our hearts, desire, and delight. The accommodations were great, although I’m sure we did not use everything listed in the advertisement. It was too cold for the pool, but the view was beautiful.. The only reason we held back one star was because the view would’ve been spectacular if the windows had been cleaned. We did have to dust one of the rooms down and floor boards because we had kids with...
The price is AED 1,749
AED 4,190 total
includes taxes & fees
13 Feb - 14 Feb
Resort Style Ranch/infinity pool for family

Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER

9.0 out of 10, Wonderful, (66)
"We had a great time with 3 families! Great way to start the new year. Lots of memories were created!"
Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER

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 AED 2,200
AED 4,576 total
includes taxes & fees
9 Feb - 10 Feb
Hacienda-In center of Temecula Wine Country

Villa Artemis - Luxurious Villa located in Temecula's Wine Valley

10.0 out of 10, Exceptional, (14)
"House was gorgeous. Loved how private it was. We will definitely go back for a staycation. I got married in Temecula & my family stayed there for the weekend & my husband and I spent one night there to recover from our wedding. It was perfect."
Villa Artemis - Luxurious Villa located in Temecula's Wine Valley

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

9.8 out of 10, Exceptional, (36)
"Would hope that owners would install grab bars for those of us who require them"
Via del Sur by AvantStay | Private Spanish Villa w/ Views | Walk to Wineries!

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

Beautiful Villa located in Temecula Wine Country

9.2 out of 10, Wonderful, (18)
"Overall we thoroughly enjoyed our stay. I would give it a 5 star if it wasn't for the lack or supplies in the laundry area, the lack of cleanliness outside the pool area, and the lack of attention to details. The major parts of the home and amenities were excellent as well as location. "
Beautiful Villa located in Temecula Wine Country

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

10.0 out of 10, Exceptional, (26)
"We stayed for a week with a group of 16. The house and yard, and games room were great. The host, Eric, is easy to reach, cares about his guests, and accommodates requests. "
Grand Lux II - Luxury Resort Pool Villa - Close to Wineries, Beaches, Temecula

Colina by AvantStay | Private Mountain Top Oasis w/ Pool, Hot Tub, Putting Green

9.8 out of 10, Exceptional, (7)
"We had 14 adults and there was plenty of room for us all. The upstairs room was great for the girl cousins to spread out and have their own bath. The space was amazing and the view spectacular! We didn't get to enjoy the hot tub as anticipated due to the power outage and not heating up, so that was disappointing. The power outage was not the fault of the owner and only lasted the first day of our trip. We made the best of it and the property manager did their best to accommodate during the...
Colina by AvantStay | Private Mountain Top Oasis w/ Pool, Hot Tub, Putting Green

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
9 Feb - 10 Feb
Villa 5B/3B with pool/spa/mini golf putting

Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views

8.8 out of 10, Excellent, (6)
"We had an awesome time. The house was beautiful. It had everything we need. Plenty of towels and the extra foams for mattress was very helpful. It’s very spacious. Everything was great. Easy to enter , the only thing we couldn’t figure out were the lights in the backyard. We knew it was controlled by the inside panel but we couldn’t get them to turn on. "
Warhol by AvantStay | Expansive Estate | Stunning Wine Cty Views

Burgundy by AvantStay | Basketball Crt, Pool, Hot Tub, Outdoor Kitchen!

9.6 out of 10, Exceptional, (14)
"Great home with many rooms and plenty of space"
Burgundy by AvantStay | Basketball Crt, Pool, Hot Tub, Outdoor Kitchen!

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
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (37)
"This casita was the most perfect place for me to stay. The host, Elizabeth, sure packs a punch in the casita with everything you could possibly need. Relaxing, beautiful, quiet and safe. Elizabeth was very communicative before my arrival and during my stay. Very responsive. I would definitely stay here again, over and over. Thank you Elizabeth and VRBO for offering this casita. "
The price is AED 213
AED 491 total
includes taxes & fees
9 Feb - 10 Feb
1/Bed Room Casita-Suite with Private Entrance

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (35)
"We booked Chateau Vino to celebrate my mom’s 90th birthday. We wanted a home that fit our whole family comfortably. The house is amazing and having space to relax, eat, and enjoy the outdoors with seating for all was perfect. We had a wonderful time and hope to return again. "
Chateau Vino - French Style Chalet

Sip and Swim Just Minutes From Temecula's Wine Country

10.0 out of 10, Exceptional, (18)
"Loved it. Very easy to communicate with the owner. The backyard looks like a tropical oasis. Very easy checking in & out process. clean & roomy. Several board games to choose from. "
Sip and Swim Just Minutes From Temecula's Wine Country
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

Why book your villa in Winchester with Expedia?
Reserving a villa in Winchester is as easy as deciding on your travel dates and selecting a place that suits your style. Looking for something inexpensive or upscale, or a stay that also includes a pool and free WiFi? Use Expedia’s search filters to narrow your results and find the perfect fit.
How can I find cheap villas in Winchester?
A fantastic way to locate cheap villas in Winchester is with Expedia’s convenient filter tool. Refine your search by amenities, star rating and budget to secure unbeatable bargains in only a few clicks.