Photo by Betsy Wood

Winchester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Winchester

Outdoor dining
1 Bed Room Casita-Suite with Private Entrance
1 Bed Room Casita-Suite with Private Entrance
9.8 out of 10, Exceptional, (55)
"Super comfortable and neat space to stay for 3 days! My host was extremely hospitable and answered my questions nearly as quickly as I wrote them!! Highly recommend I would stay again!!!"
United States
Lynette
The price is ￥4,749
￥16,530 total
includes taxes & fees
Oct 28 - Oct 29
1 Bed Room Casita-Suite with Private Entrance
Fridge, microwave, oven, stovetop
•Charming One-Level Home • Feels Like Home
•Charming One-Level Home • Feels Like Home
The price is ￥55,024
￥84,873 total
includes taxes & fees
Oct 26 - Oct 27
•Charming One-Level Home • Feels Like Home
Property grounds
The Pony Experience Farm Stay! 501c3
The Pony Experience Farm Stay! 501c3
8.4 out of 10, Very Good, (5)
"Me and my daughter couldn’t have asked for a better experience. Hosts were attentive to us and the animals were AMAZING to be around. Horses, peacocks, dogs, fowl, all very welcoming and happy to have guests around. I just wish…nothing. It was great. Very serene too."
United States
Megan
The price is ￥37,537
￥47,487 total
includes taxes & fees
Nov 6 - Nov 7
The Pony Experience Farm Stay! 501c3
Outdoor pool
Coral Tree House
Coral Tree House
3.0 star property
10.0 out of 10, Exceptional, (19)
"Michelle and Greg were great host they very kind and generous. Very knowledgeable about the surrounding area. Absolutely lovely place to stay."
United States
Jesus
The price is ￥24,120
￥35,848 total
includes taxes & fees
Oct 23 - Oct 24
Coral Tree House
The Motorist Choice: Queen Bed and Hot Shower, Smoking & Non-smoking Room | 1 bedroom, individually decorated, individually furnished, desk
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
9.8 out of 10, Exceptional, (22)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is ￥17,401
￥20,603 total
includes taxes & fees
Oct 23 - Oct 24
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3 outdoor pools, pool umbrellas, sun loungers
The Cottages at Golden Village Palms RV Resort
The Cottages at Golden Village Palms RV Resort
3.0 star property
9.2 out of 10, Wonderful, (75)
"This is a hidden jem in Hemet love the pools the grounds are well maintained and I will definitely be staying here again"
United States
mary
The price is ￥22,763
￥26,769 total
includes taxes & fees
Oct 26 - Oct 27
The Cottages at Golden Village Palms RV Resort
Fridge, microwave, oven, stovetop
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
2.0 star property
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay , host was great and location also very calm and beautiful, recommend 10/10"
United States
Christy M.
The price is ￥33,919
￥85,702 total
includes taxes & fees
Oct 23 - Oct 24
BEAUTIFUL 2 STORY HOUSE IN MORENO VALLEY
Property grounds
Secluded mystical cabin in Idyllwild-Pine Cove
Secluded mystical cabin in Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (4)
"Lots of wildlife, very rustic cabin experience "
United States
Robert H.
The price is ￥9,497
￥23,818 total
includes taxes & fees
Oct 28 - Oct 29
Secluded mystical cabin in Idyllwild-Pine Cove
A heated pool
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
2.0 star property
9.0 out of 10, Wonderful, (12)
"Excellent house and location, great host communication."
United States
Jed H.
The price is ￥18,118
￥62,652 total
includes taxes & fees
Oct 26 - Oct 27
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
Exterior
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
10.0 out of 10, Exceptional, (39)
"just a quick one night stay- it was great"
United States
Rick M.
The price is ￥15,860
￥34,019 total
includes taxes & fees
Nov 3 - Nov 4
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Suite | 2 bedrooms, Internet
Dog Friendly A-frame Hot Tub Nature Views
Dog Friendly A-frame Hot Tub Nature Views
2.0 star property
The price is ￥23,646
￥51,083 total
includes taxes & fees
Oct 26 - Oct 27
Dog Friendly A-frame Hot Tub Nature Views
Fridge, microwave, oven, stovetop
Hacienda de Paz - Estate of Peace
Hacienda de Paz - Estate of Peace
2.0 star property
10.0 out of 10, Exceptional, (5)
"We were blown away with this beautiful property! Yami was the perfect host! I would 100% recommend staying at Hacienda de Paz."
United States
Daniel V.
The price is ￥81,405
￥150,901 total
includes taxes & fees
Oct 26 - Oct 27
Hacienda de Paz - Estate of Peace
Property grounds
Cactus Garden Cottage…Best Location!!
Cactus Garden Cottage…Best Location!!
10.0 out of 10, Exceptional, (50)
"A sweet and perfect cottage! We had looked into overpriced hotels in Temecula for a wedding but ultimately decided to stay here and so glad we did! It's very private and charming and the host thought of all the touches to make our stay great."
United States
Kelly
The price is ￥14,924
￥25,627 total
includes taxes & fees
Oct 23 - Oct 24
Cactus Garden Cottage…Best Location!!
House (1 Bedroom) | Interior
Fallbrook Airplane Home w/ Fire Pit & Mtn Views!
Fallbrook Airplane Home w/ Fire Pit & Mtn Views!
3.0 star property
The price is ￥45,828
￥77,308 total
includes taxes & fees
Oct 26 - Oct 27
Fallbrook Airplane Home w/ Fire Pit & Mtn Views!
Exterior
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
9.6 out of 10, Exceptional, (25)
"We stayed there the whole trip. Never even went into town. The property has great amenities and we brought our food and cooked easily. Traeger gril is a definite plus! Would book it again."
United States
david W.
The price is ￥19,748
￥50,516 total
includes taxes & fees
Oct 23 - Oct 24
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Exterior detail
Wine Country Working Wool Sheep Farm Stay; Hay Barn Cottage
Wine Country Working Wool Sheep Farm Stay; Hay Barn Cottage
3.0 star property
10.0 out of 10, Exceptional, (2)
"Namaste farms is a gem in the middle of wine country! It is my favorite place to stay, wind down and relax! Love that I can drive 4 hours to wine country but being able to stay here is the cherry on top! If you’re looking for quiet, comfortable place this is it! Love Namaste Farms, will definitely stay again!"
United States
Callie F.
The price is ￥41,456
￥61,087 total
includes taxes & fees
Oct 23 - Oct 24
Wine Country Working Wool Sheep Farm Stay; Hay Barn Cottage
Property grounds
Twin Rock Tree House - Vintage Cabin
Twin Rock Tree House - Vintage Cabin
9.8 out of 10, Exceptional, (27)
"We enjoyed our weekend stay at Twin Rocks. It’s a lovely place, very clean and such nice touches. I enjoyed sitting outside in the front and on the back porch, and all the light coming in from the many windows."
United States
Eve R.
The price is ￥20,053
￥39,778 total
includes taxes & fees
Nov 11 - Nov 12
Twin Rock Tree House - Vintage Cabin
Terrace/patio
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
9.8 out of 10, Exceptional, (8)
"Property was spacious for two, listing was very accurate. Clean and comfortable casita with an accommodative owner. Would recommend to anyone looking for a place to stay."
United States
Jacob W.
The price is ￥14,924
￥19,748 total
includes taxes & fees
Oct 23 - Oct 24
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
Property grounds
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
10.0 out of 10, Exceptional, (1)
"We were lucky to find this beautiful place when the weather turned and camping was no longer an option. Our host was very accomodating and was able to allow us to check in early to a very clean, spacious private cabin that is more like a light house, with amazing views in the Pine Cove area. Wonderful 5 star stay! "
United States
Susan M.
The price is ￥17,728
￥39,626 total
includes taxes & fees
Oct 23 - Oct 24
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Property grounds
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
9.8 out of 10, Exceptional, (9)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
United States
Chloe D.
The price is ￥37,688
￥52,537 total
includes taxes & fees
Oct 27 - Oct 28
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Ayres Hotel & Spa Moreno Valley

Ayres Hotel & Spa Moreno Valley

10/10 Excellent
"Best hotel beds I’ve had. Pool and spa aren’t easily findable could use better signage. "
Jennifer 1-night trip
Posted 3 days ago
Ayres Hotel & Spa Moreno Valley

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near well known sights in Winchester, or you can choose a secluded option if you're looking for relaxation. Winchester is known for its wineries and coffeehouses. Make sure you have time to check out the bars while you're in the area.

What's the top vacation rental in Winchester?

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!: Visitors give good reviews to this Winchester vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

Choose from 34 Expedia vacation rentals in Winchester for a memorable vacation.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Orange Empire Railroad Museum, or get out into nature at a spot like Diamond Valley Lake Marina. K1 Circuit and Pechanga Resort & Casino are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private properties you can stay in for a short or long stay in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.