Title: Winchester Villas from CA $398 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000429004.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000429004.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d3000429004.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000429004.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000429004.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/168795653f137890cc5c8b094f57b3d3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Betsy Wood # Search Winchester Villa Rentals from CA $398 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Villas ![A heated pool](https://images.trvl-media.com/lodging/108000000/107600000/107597500/107597438/a11e8f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107600000/107597500/107597438/4a6ca7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/108000000/107600000/107597500/107597438/f59c7311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107600000/107597500/107597438/1ebc209e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub Fallbrook 9.0/10 Wonderful (12) "Excellent house and location, great host communication." CA $188 CA $601 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fallbrook-Hotels-Luxury-5-Bedroom-Villa-W-Pool.h107597438.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35840000/35837300/35837296/39bc6cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35840000/35837300/35837296/50991019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, jetted tub, hair dryer, towels](https://images.trvl-media.com/lodging/36000000/35840000/35837300/35837296/9c65890c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/36000000/35840000/35837300/35837296/ca62627b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private secluded Hideaway above the lights Fallbrook 7.2/10 Good (5) "Very nice experience. Beautiful views. Cute and quaint! Very nice owner." CA $315 CA $398 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Fallbrook-Hotels-Private-Secluded-Hideaway-Above-The-Lights.h35837296.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/109000000/108900000/108896000/108895978/e7eed3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/109000000/108900000/108896000/108895978/70e319fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/109000000/108900000/108896000/108895978/221a8460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108900000/108896000/108895978/5c8d1754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Priv. Resort! Mountain Views Oasis- Heated Pool & Spa, Game Rm, Temecula-8 miles Fallbrook 10/10 Exceptional (9) "Home is beautiful, safe and quiet. Views are perfect ! " CA $954 CA $1,428 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Fallbrook-Hotels-Modern-Luxury-Villa-Mtn-Views.h108895978.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96100000/96093600/96093554/262fbcff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/97000000/96100000/96093600/96093554/a4963931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96100000/96093600/96093554/a9bad5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96100000/96093600/96093554/e7f41934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Views Villa with Spa / Close to Winery GlenOak Hills 10/10 Exceptional (1) "The bedrooms were spacious and clean. The house was inviting and the outdoor area was massive with amazing views of the valley. The host was responsive and kind. We had a nice stay. " CA $579 CA $1,519 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Temecula-Hotels-Amazing-Views-Villa-Spa-Games-BBQ-Close-To-Winery.h96093554.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89690000/89681600/89681526/706f25a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89690000/89681600/89681526/e3e4672a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89690000/89681600/89681526/1a1bda12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89690000/89681600/89681526/8914aca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 5B/3B with pool/spa/mini golf putting Valle De Los Caballos 9.2/10 Wonderful (33) "We had a great time this weekend. It was great for our girls trip… super spacious. " CA $495 CA $1,400 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Temecula-Hotels-Villa-5B3B-With-Poolspamini-Golf-Putting.h89681526.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/73000000/72040000/72036500/72036412/9067e8da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72040000/72036500/72036412/109bbcb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72040000/72036500/72036412/e0594f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/73000000/72040000/72036500/72036412/56461937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★The Iron Mansion 9 Acre Luxurious Private Resort 12000 ft Event Space! ★ Cross Creek 10/10 Exceptional (31) "Great facility, chairs and tables on site for a 40 person wedding. Beautiful views and options for a fun weekend. " CA $825 CA $1,984 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Temecula-Hotels-The-Iron-Mansion-9-Acre-Luxurious-Private-Resort-12000-Ft-Event-Space.h72036412.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014564/399523b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014564/5adeae03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014564/b1589956_edited_b3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014564/a8de7f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5BR/4Bth Entire Grand Estate near Winery Fallbrook Fallbrook 8.4/10 Very good (6) "Had a great experience staying at this property. Huge land and space and very secluded from other neighbors. " CA $189 CA $623 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Fallbrook-Hotels-3-Acre-Estate-With-View.h112014564.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87570000/87568600/87568548/95f9f88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/88000000/87570000/87568600/87568548/b38fe057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87570000/87568600/87568548/da34f217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87570000/87568600/87568548/03bd414a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa with indoor pool in Temecula wine country-VRBO Valle De Los Caballos 9.2/10 Wonderful (35) "Perfect place for our short weekend getaway. Stayed for 3 nights. Home had plenty of room inside and out. GreatCommunication with management. " CA $629 CA $1,568 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Temecula-Hotels-Villa-With-Indoor-Pool-In-Temecula-Wine-Country-VRBO.h87568548.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/85000000/84520000/84519800/84519760/74fa9827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/85000000/84520000/84519800/84519760/d5b6229c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84520000/84519800/84519760/7aace6dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84520000/84519800/84519760/f60b2970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort Style Ranch/infinity pool for family Valle De Los Caballos 9.2/10 Wonderful (36) "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. " CA $581 CA $1,469 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Temecula-Hotels-Resort-Style-Ranchinfinity-Pool-For-Family.h84519760.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66710000/66702900/66702836/83dcd59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66710000/66702900/66702836/fe523fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66710000/66702900/66702836/66727842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66710000/66702900/66702836/99b2917f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### French Wine Country Estate with Infinity Pool+Wine Tasting Room Valle De Los Caballos 9.4/10 Exceptional (30) "Easy communication with owner and beautiful home. The backyard was the best part. " CA $2,155 CA $3,304 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Temecula-Hotels-French-Wine-Country-Estate-With-Infinity-PoolWine-Tasting-Room.h66702836.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117516300/117516263/23f31408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117516300/117516263/136f646c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117520000/117516300/117516263/53e16ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117520000/117516300/117516263/6eed3c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing views countryside Luxe Fallbrook CA $980 CA $2,031 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Fallbrook-Hotels-Amazing-Views-Countryside-Luxe.h117516263.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29®ionId=3000429004&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Villas.d3000429004-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Villas.d3000429004-aaVillas.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Hilton Garden Inn Temecula, CA](//images.trvl-media.com/lodging/71000000/70410000/70404500/70404430/df624541_y.jpg) ### Hilton Garden Inn Temecula, CA 10/10 Excellent "Property is newer than others. Not a lot of parking in the basement. Stayed in a King deluxe and the room is huge." [](https://expedia.ca/Temecula-Hotels-Hilton-Garden-Inn-Temecula.h70404430.Hotel-Information) ![Ayres Hotel & Spa Moreno Valley](//images.trvl-media.com/lodging/4000000/3540000/3538400/3538336/9a8447f3_y.jpg) ### Ayres Hotel & Spa Moreno Valley 10/10 Excellent "Really enjoy staying here. Clean comfortable rooms. Friendly staff. Great breakfast options" [](https://expedia.ca/Riverside-Hotels-Ayres-Hotel-Spa-Moreno-Valley.h3538336.Hotel-Information) ![Tahquitz Pines Retreat](//images.trvl-media.com/lodging/101000000/100150000/100140100/100140075/ad7ea05d_y.jpg) ### Tahquitz Pines Retreat 10/10 Excellent "The pickleball courts were a big hit. The grounds are spacious, clean, and filled with beautiful trees. The staff were friendly and helpful. My bed was comfortable and the room very clean." [](https://expedia.ca/Idyllwild-Hotels-Tahquitz-Pines-Retreat.h100140075.Hotel-Information) ![Signature Temecula](//images.trvl-media.com/lodging/1000000/10000/3900/3867/b684d953_y.jpg) ### Signature Temecula 10/10 Excellent "Clean and comfortable " [](https://expedia.ca/Temecula-Hotels-Signature-Temecula.h3867.Hotel-Information) ![Temecula Creek Inn](//images.trvl-media.com/lodging/1000000/30000/25500/25488/68f2c541_y.jpg) ### Temecula Creek Inn 10/10 Excellent "Beautiful property, friendly staff and wonderful food from the restaurant!" [](https://expedia.ca/Temecula-Hotels-Temecula-Creek-Inn.h25488.Hotel-Information) ![Staybridge Suites Temecula Wine Country by IHG](//images.trvl-media.com/lodging/64000000/63120000/63112100/63112033/98588603_y.jpg) ### Staybridge Suites Temecula Wine Country by IHG 10/10 Excellent "Great property. Location close to everything and the hotel had wonderful options. The continental breakfast was spectacular. I really was impressed by this. Downside, a few of the hotel rooms had visible damage on the doors and the bathrooms seemed to have water damage. Beds were comfy and the pool was quite nice. " [](https://expedia.ca/Temecula-Hotels-Staybridge-Suites-Temecula-Wine-Country.h63112033.Hotel-Information) ![Murrieta Hot Springs Resort](//images.trvl-media.com/lodging/102000000/101390000/101380300/101380271/2b0b7a85_y.jpg) ### Murrieta Hot Springs Resort 10/10 Excellent "Beautiful place. I love the fact we can stay there overnight and get to enjoy the next day" [](https://expedia.ca/Murrieta-Hotels-Murrieta-Hot-Springs-Resort.h101380271.Hotel-Information) ![Studio 6 Suites Perris, CA](//images.trvl-media.com/lodging/1000000/20000/13500/13490/788a1027_y.jpg) ### Studio 6 Suites Perris, CA 10/10 Excellent "very nice hotel clean and comfortable " [](https://expedia.ca/Perris-Hotels-Perris-Hotel-Inn-Suites.h13490.Hotel-Information) ![Pala Casino Spa And Resort](//images.trvl-media.com/lodging/2000000/1080000/1072000/1071947/4db651de_y.jpg) ### Pala Casino Spa And Resort 10/10 Excellent "Would like to see more restaurant options open 24 hours" [](https://expedia.ca/Temecula-Hotels-Pala-Casino-Spa-And-Resort.h1071947.Hotel-Information) ## Find out more about Winchester ## Winchester Villas information | Number of reviews | 189 | | --- | --- | | Accommodation | 115 Villas | | Lowest Price | CA $398 | | Highest Price | CA $2,031 | ## 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. 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