Photo by Betsy Wood

Search Villas in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Villas in Winchester

Stunning Hilltop Villa | Pool | Panoramic Views
Fridge, microwave, oven, stovetop

Stunning Hilltop Villa | Pool | Panoramic Views

The price is AED 2,596
AED 4,088 total
includes taxes & fees
22 Jun - 23 Jun
Stunning Hilltop Villa | Pool | Panoramic Views
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, (33)
"We loved the house, it was beautiful and even nicer in person. Loved the chefs kitchen and hot tub! Only wish the rooms had a few more curtains so it didn’t get as bright in the morning but we had a wonderful stay. We could stay again. Great house for groups or a big family vacation. "
Resort Style Ranch/infinity pool for family
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, (31)
"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."
Villa with indoor pool in Temecula wine country-VRBO
Villa 5B/3B with pool/spa/mini golf putting
Outdoor pool, a heated pool

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

9.4 out of 10, Exceptional, (24)
"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!"
Villa 5B/3B with pool/spa/mini golf putting
Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER
Outdoor pool

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

9.0 out of 10, Wonderful, (68)
"My family and friends recently stayed here and this property was so beautiful and the perfect getaway. It had tons of stuff for us to do like board games, spa, waterslide, and soccer nets. The host was very helpful and we are so grateful we had a nice stay! Can’t wait to come again in the summer! "
The price is AED 4,774
AED 6,699 total
includes taxes & fees
9 Jul - 10 Jul
Relaxing Wine Country Estate w/BAR+SPA+POOL+BBQ+VBALL+SOCCER
Hacienda-In center of Temecula Wine Country
Outdoor dining

Hacienda-In center of Temecula Wine Country

9.8 out of 10, Exceptional, (23)
"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 2,997
AED 5,618 total
includes taxes & fees
21 Jul - 22 Jul
Hacienda-In center of Temecula Wine Country
Amazing views countryside Luxe
Terrace/patio

Amazing views countryside Luxe

The price is AED 2,020
AED 3,985 total
includes taxes & fees
23 Jun - 24 Jun
Amazing views countryside Luxe
Amazing view
Terrace/patio

Amazing view

The price is AED 2,057
AED 3,610 total
includes taxes & fees
18 Jul - 19 Jul
Amazing view
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, (2)
"Had a great experience staying at this property. Huge land and space and very secluded from other neighbors. "
The price is AED 879
AED 1,948 total
includes taxes & fees
22 Jun - 23 Jun
3-Acres Estate, 3000 sqft, near Winery in Fallbroo
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, (4)
"Home is beautiful, safe and quiet. Views are perfect ! "
The price is AED 3,121
AED 4,522 total
includes taxes & fees
21 Jul - 22 Jul
Priv. Resort! Mountain Views Oasis- Heated Pool & Spa, Game Rm, Temecula-8 miles
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
9.4 out of 10, Exceptional, (9)
"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 1,209
AED 2,331 total
includes taxes & fees
25 Jun - 26 Jun
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,
Private secluded Hideaway above the lights
Terrace/patio

Private secluded Hideaway above the lights

7.2 out of 10, Good, (5)
"Very nice experience. Beautiful views. Cute and quaint! Very nice owner."
The price is AED 826
AED 1,050 total
includes taxes & fees
23 Jun - 24 Jun
Private secluded Hideaway above the lights
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your villa in Winchester with Expedia?
Expedia makes it a cinch to find your dream villa in Winchester. Traveling with the kids? Use our handy filters to search for stays with perks like a swimming pool. If you have a fixed budget, choose how much you want to spend and your preferred star rating. We'll help you find the right fit that suits your taste and style.
How can I find cheap villas in Winchester?
Expedia can help you search for cheap villas in Winchester. Use the filter tool to select star rating, budget and amenities to refine your search and find a great place to stay in a matter of clicks.