Photo by Betsy Wood

Search Condo Rentals 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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 10 Condo Rentals in Winchester with updated reviews, rates, and availability.

Weekend Wine Getaway
Fridge, microwave, stovetop, dishwasher

Weekend Wine Getaway

9.2 out of 10, Wonderful, (7)
"We enjoyed our stay at Temecula - a first for us! The place was clean, great to have 2 larger bedrooms with their own ensuite bathrooms. Good location, great response from landlord."
Weekend Wine Getaway
Wine Country Condo 1 bed 1 bath
Fridge, microwave, oven, stovetop

Wine Country Condo 1 bed 1 bath

9.6 out of 10, Exceptional, (41)
"Perfect property for a couples long weekend visit to Temecula’s wonderful wineries and fun downtown. Comfortable, quiet, clean and polite and responsive host. Highly recommended!"
Wine Country Condo 1 bed 1 bath
Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green
Interior

Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green

3.5 star property
10.0 out of 10, Exceptional, (1)
"Loved everything about this place.Very spacious, lots of activities included. Especially the relaxing view from hill top. Master bedroom also had an amazing view. Highly recommend "
Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green
Hidden Paradise in the Heart of the City
Private kitchen

Hidden Paradise in the Heart of the City

Hidden Paradise in the Heart of the City
Wilson Creek Manor By Avantstay Sleeps 10! Amazing Estate w/ Pool & Game Room
Interior

Wilson Creek Manor By Avantstay Sleeps 10! Amazing Estate w/ Pool & Game Room

3.5 star property
Wilson Creek Manor By Avantstay Sleeps 10! Amazing Estate w/ Pool & Game Room
Beautiful Family Home Sleeps 6
Smart TV

Beautiful Family Home Sleeps 6

Beautiful Family Home Sleeps 6
Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!
Terrace/patio

Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!

3.5 star property
Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!
Room with private entrance private bathroom
Property grounds

Room with private entrance private bathroom

Room with private entrance private bathroom
Condo
Property grounds

Condo

Condo
Corporate 30 day rental
Fridge, microwave, stovetop, dishwasher

Corporate 30 day rental

Corporate 30 day rental
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
Sign in
Sign up, it's free

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.

Frequently asked questions

Why book your condo in Winchester with Expedia?
Reserving a condo in Winchester is as simple as clicking on your travel dates and choosing the option that suits your needs. On the lookout for something budget friendly or upmarket, or a stay that also includes a pool? Use Expedia’s search filters to further narrow your search results and find the perfect fit.
How can I find cheap condos in Winchester?
With Expedia’s helpful filter tool, comparing cheap condos in Winchester is a breeze. To find properties that are very pocket friendly, narrow your search results by budget, star rating and amenities.