Title: Winchester Vacation Home Rentals from CA $253: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000435714.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester vacation homes ![Exterior](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/9ef3ff50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/269b2632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/00d407ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/3b40112f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS! [](https://www.expedia.ca/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information) Bluffs 10/10 Exceptional (58 reviews) "Beautiful place, highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony S. CA $244 CA $293 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/bdc25008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, toilet paper](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/455305f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/fc67e1b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/fe81fa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area [](https://www.expedia.ca/Pleasant-Hill-Hotels-Charming-2-Bedroom-Barnloft-On-Hobby-Farm-In-Pleasant-Hill-Pittsfield-Area.h120110900.Hotel-Information) Pleasant Hill CA $176 CA $253 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Pleasant-Hill-Hotels-Charming-2-Bedroom-Barnloft-On-Hobby-Farm-In-Pleasant-Hill-Pittsfield-Area.h120110900.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=2026-03-01&endDate=2026-03-02®ionId=3000435714&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_3000435714) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CABIN) ![](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-Private-Vacation-Homes.d3000435714-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Private-Vacation-Homes.d3000435714-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "Clean comfy spacious rooms. Great staff" [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites South Jacksonville 10/10 Excellent "Clean, quiet and comfortable. Have stayed many times and will continue. " [](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c_y.jpg) ### Green Acres Hotel 10/10 Excellent "Highly recommend. Great staff. Friendly customer service. Would stay again for sure. " [](https://expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Audrey's Abode ](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c_y.jpg) ### Audrey's Abode 10/10 Excellent "If you love the country life, or have lived in the country for awhile, this place will bring you right back to it. Absolutely amazing, in all ways. Will be back again. Thank you! " [](https://expedia.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Clean room and great breakfast." [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "The pool was warm!! The room was nice and clean .. The water pressure in the showers along with the soap that was free was amazing .. for a cheap rate you couldn’t beat this hotel " [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "Clean room. Great friendly staff. " [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Monroe Street Suites](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae_y.jpg) ### Monroe Street Suites 10/10 Excellent "Great accomodations and concept for a small town. Much better than staying in a low budget chain hotel." [](https://expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c_y.jpg) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. 10/10 Excellent "Kevin was an excellent host and the house on the prairie was exactly what we needed after a long day of travel. We were surprised with fresh baked cookies upon arrival.The house was very cozy and walking the trails of the prairie was great for our pup. We would definitely stay here again the future!" [](https://expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 58 | | ----------------- | ---------------- | | Accommodation | 7 Vacation Homes | | Lowest Price | CA $253 | | Highest Price | CA $293 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Alsey Hotels ](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Arcadia ](https://www.expedia.ca/Arcadia-Apartments.d553248635975871406-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Arenzville ](https://www.expedia.ca/Arenzville-Cabins.d3000346095-aaCabins.Travel-Guide-Accommodation) - [Arenzville Hotels ](https://www.expedia.ca/Arenzville-Hotels.d3000346095.Travel-Guide-Hotels) - [Luxury Hotels in Ashland ](https://www.expedia.ca/Ashland-Hotels-Luxury-Hotel.0-0-d3000420824-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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