Title: Winchester Vacation Home Rentals from CA $235: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6046207.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) # Winchester Vacation Rentals - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6046207&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 four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102445100/102445023/055796df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102450000/102445100/102445023/w1024h455x0y114-9cc96f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102450000/102445100/102445023/2756ee3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102450000/102445100/102445023/w1024h454x0y115-790feae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cardinal Cottage - 2 bedroom cozy home Muncie 9.6/10 Exceptional (29) "Very clean and easy weekend stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ally B. CA $126 CA $235 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Muncie-Hotels-Cardinal-Cottage-2-Bedroom-Cozy-Home.h102445023.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95510000/95506300/95506257/w905h683x59y0-2af7acef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/96000000/95510000/95506300/95506257/w508h683x258y0-c2215ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95510000/95506300/95506257/w692h683x167y0-1bb538e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95510000/95506300/95506257/w632h683x196y0-0369056d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boho Bungalow off Main-one block from Lovely Park Richmond 9.0/10 Wonderful (13) "Lovely house, easy check-in, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather S. CA $133 CA $250 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Richmond-Hotels-Boho-Bungalow-Off-Main-One-Block-From-Lovely-Park.h95506257.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106820000/106812900/106812845/ae7889b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, travel crib, WiFi](https://images.trvl-media.com/lodging/107000000/106820000/106812900/106812845/f0cb3572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106820000/106812900/106812845/6184ce26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106820000/106812900/106812845/6580be7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room. Greenville 9.0/10 Wonderful (8) "This is a beautiful home with exceptional amenities. Is just about the closest home to the fairgrounds. Does need a gas grill.Thank you for letting us stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonia E. CA $216 CA $343 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Greenville-Hotels-Charming-3-Bedroom-House-In-Tranquil-Greenville-With-WiFi.h106812845.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/111000000/110690000/110682000/110681924/cb34ab95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/111000000/110690000/110682000/110681924/cd5ed359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110690000/110682000/110681924/1cfd5414.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110690000/110682000/110681924/b48e6205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retro Home Close to Campus Muncie 9.8/10 Exceptional (9) "Nice property no hassel stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald D. CA $189 CA $415 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Muncie-Hotels-Retro-Home-Close-To-Campus.h110681924.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103850000/103842500/103842461/5eab9d5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/104000000/103850000/103842500/103842461/8d5c0d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103842500/103842461/acf8a0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103842500/103842461/7dd27afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home! Prime Location! Dog-Friendly! Richmond 9.8/10 Exceptional (13) "Great house! Just what we needed and in an amazing Richmond neighborhood. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason S. CA $220 CA $461 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Richmond-Hotels-Charming-Home-Close-To-All-Richmond-Has-To-Offer-Dog-Friendly.h103842461.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115590000/115587500/115587430/a73b76bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/116000000/115590000/115587500/115587430/81fbe85c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115590000/115587500/115587430/7f45e2af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115590000/115587500/115587430/16a4aa3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house with AC, WiFi in Greenville Greenville 9.0/10 Wonderful (8) "Nice place good location. Would highly recommend to anyone." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven M. CA $219 CA $346 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Greenville-Hotels-Charming-3-Bedroom-House-With-AC.h115587430.Hotel-Information) ![8 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90260000/90254300/90254204/3a569ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90260000/90254300/90254204/2682307b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90254300/90254204/w1125h772x0y6-3f1c75dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90260000/90254300/90254204/659a7705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westcott Mansion with Pickleball Court & Huge Gazebo Richmond 9.8/10 Exceptional (35) "We had the best time. House was gorgeous and unique. Perfect place for our group as everyone had their own room and their own bed! Would absolutely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan H. CA $231 CA $465 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Richmond-Hotels-Westcott-Mansion-With-Pickleball-Court-Huge-Gazebo.h90254204.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119610000/119609900/119609846/ee077b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119610000/119609900/119609846/957a628e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119610000/119609900/119609846/dad3b525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119610000/119609900/119609846/cb251a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus Muncie 10/10 Exceptional (1) "House is cute - loved all the wood floors although they're noisy. beds were comfortable. only stayed one night but it was walkable back and forth to campus so that was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abi Z. CA $209 CA $304 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Muncie-Hotels-Family-Friendly-Home.h119609846.Hotel-Information) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122580000/122574000/122573970/78dcc6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122580000/122574000/122573970/0c8850e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122580000/122574000/122573970/ea2910c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/123000000/122580000/122574000/122573970/7b3d92cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State Muncie CA $111 CA $273 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Muncie-Hotels-Charming-2-Bedroom-House-In-Muncie-With-Bunk-Game-Room-Close-To-Ball-State.h122573970.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113760000/113751300/113751269/8b039b3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113760000/113751300/113751269/f951338b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113760000/113751300/113751269/c53a061d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113760000/113751300/113751269/b5a5139f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14 Fort Recovery 10/10 Exceptional (5) "We had an AMAZING time at Elm & Ivy!! What a beautiful venue for a chill bachelorette party!! There were so many perfect little touches that added to our stay. Highly recommend- we already talked about coming back again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tony & Cindy M. CA $529 CA $605 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Fort-Recovery-Hotels-Fort-Recoverys-Historic-1940s-Chapel-With-Speakeasy-Hideaway-Sleeps-10.h113751269.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39090000/39083800/39083718/w1080h1285x0y0-80386403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39090000/39083800/39083718/w1440h949x0y0-2d5c1027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/40000000/39090000/39083800/39083718/80937ecf_edited_fc9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39090000/39083800/39083718/w1440h948x0y0-2d755dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country living 4 Bedroom House Delaware Township CA $1,257 CA $1,608 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Albany-Hotels-Country-Living-4-Bedroom-House.h39083718.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=2025-12-17&endDate=2025-12-18®ionId=6046207&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6046207) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=CABIN) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=CONDO) ![](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.d6046207-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.d6046207-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Comfort Suites](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/d689bf19_y.jpg) ### Comfort Suites 10/10 Excellent "Room was very clean. The staff was very friendly and helpful. Breakfast was hot and tasty. " [](https://expedia.ca/Richmond-Hotels-Comfort-Suites.h92418479.Hotel-Information) ![Baymont by Wyndham Richmond I-70](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944_y.jpg) ### Baymont by Wyndham Richmond I-70 10/10 Excellent "Everyone was friendly, the rooms were clean. I will say the pictures make it look nicer than it is but still a great stay!" [](https://expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Hampton Inn & Suites Richmond, IN](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/1e53a5db_y.jpg) ### Hampton Inn & Suites Richmond, IN 10/10 Excellent "Very nice" [](https://expedia.ca/Richmond-Hotels-Hampton-Inn-Suites-Richmond.h1590037.Hotel-Information) ![Courtyard Muncie at Horizon Convention Center](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/6aef882b_y.jpg) ### Courtyard Muncie at Horizon Convention Center 10/10 Excellent "Excellent!" [](https://expedia.ca/Muncie-Hotels-Courtyard-Muncie-At-Horizon-Convention-Center.h12755848.Hotel-Information) ![Best Western Plus Richmond Indiana I-70](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730_y.jpg) ### Best Western Plus Richmond Indiana I-70 10/10 Excellent "All was good" [](https://expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Baymont by Wyndham Muncie Near Ball State University](https://images.trvl-media.com/lodging/1000000/10000/3300/3204/39faaa1f_y.jpg) ### Baymont by Wyndham Muncie Near Ball State University 10/10 Excellent "Very nice " [](https://expedia.ca/Muncie-Hotels-Baymont-By-Wyndham-Muncie-Near-Ball-State-University.h3204.Hotel-Information) ![Quality Inn and Conference Center](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/ebc0f494_y.jpg) ### Quality Inn and Conference Center 10/10 Excellent "Clean room nice staff did not use pool" [](https://expedia.ca/Richmond-Hotels-Quality-Inn-And-Conference-Center.h25869.Hotel-Information) ![Days Inn by Wyndham Muncie -Ball State University](https://images.trvl-media.com/lodging/1000000/10000/4600/4571/edaea515_y.jpg) ### Days Inn by Wyndham Muncie -Ball State University 10/10 Excellent "Room was clean and staff was courteous!" [](https://expedia.ca/Muncie-Hotels-Days-Inn-By-Wyndham-Muncie-Ball-State-University.h4571.Hotel-Information) ![Motel 6 Richmond, IN](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/3e0f69fd_y.jpg) ### Motel 6 Richmond, IN 10/10 Excellent "We were here 4 weeks...The rooms are clean, they allow your pets as family, and it doesnt smell like animals. The staff are wonderful and respectful of your space. I would definitely stay here again. Indoor pool and hotub are also very clean. Definitely perfect for a family on a budget.. ❤️🧡 " [](https://expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 115 | | --- | --- | | Accommodation | 48 Vacation Homes | | Lowest Price | CA $235 | | Highest Price | CA $1,608 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in East Central Indiana](https://www.expedia.ca/5Star-East-Central-Indiana-Hotels.s50-0-d6233870.Travel-Guide-Filter-Hotels) - [Apartments in Albany](https://www.expedia.ca/Albany-Apartments.d553248634983410143-aaApartments.Travel-Guide-Accommodation) - [Cheap Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Cheap-Hotels.0-0-d553248634983410143-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Albany](https://www.expedia.ca/Albany-Hotels-Hotel-With-Pool.0-0-d553248634983410143-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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