Title: Winchester, IN Cottage Rentals from $323 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6046207)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6046207.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/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) ![](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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6046207&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6046207&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6046207&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6046207&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester cottages ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124960000/124955500/124955411/15e1f30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124960000/124955500/124955411/da401f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124960000/124955500/124955411/0989ae57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124960000/124955500/124955411/3557a186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pets Welcome! Quiet Economy Home w/ Spacious Yard [](https://www.expedia.com/Economy-Hotels-Pets-Welcome-Quiet-Economy-Home-W-Spacious-Yard.h124955411.Hotel-Information) Economy $291 nightly $323 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Economy-Hotels-Pets-Welcome-Quiet-Economy-Home-W-Spacious-Yard.h124955411.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.com/Hotel-Search?startDate=2026-03-19&endDate=2026-03-20®ionId=6046207&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.com/deals?rfrr=AA_SPRING_PROMO_6046207) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Indiana%2C+United+States+of+America®ionId=6046207&latLong=40.171989%2C-84.981354&adults=2&startDate=2026-06-03&d1=2026-06-03&endDate=2026-06-06&d2=2026-06-06&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d6046207-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d6046207-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![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 "Great!" [](https://expedia.com/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Comfort Suites](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/d689bf19_y.jpg) ### Comfort Suites 10/10 Excellent "The hotel was very clean. The staff are very friendly. This is where I will stay when I return to Richmond IN.!!!!" [](https://expedia.com/Richmond-Hotels-Comfort-Suites.h92418479.Hotel-Information) ![Comfort Inn & Suites Muncie Near University](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/eec57f36_y.jpg) ### Comfort Inn & Suites Muncie Near University 10/10 Excellent "Staff was gracious and generous to meet our needs and concerns. Travel was necessary but arduous due to on going medical issues. Stay was excellent." [](https://expedia.com/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) ![Hampton Inn & Suites Muncie](https://images.trvl-media.com/lodging/3000000/2050000/2041500/2041430/cdcb7601_y.jpg) ### Hampton Inn & Suites Muncie 10/10 Excellent "Everything was clean, the the was pleasant and helpful." [](https://expedia.com/Muncie-Hotels-Hampton-Inn-Suites-Muncie.h2041430.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 "Awesome. This Baymont exceeded my expectations. The room was nicely updated and very quiet. The pool and spa were relaxing after a long day. Breakfast was fantastic. Eggs made to order, biscuits and gravy, sausage, waffles, etc. Front desk and breakfast area staff were great. I definitely want to stay here again. " [](https://expedia.com/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Super 8 by Wyndham Muncie/Ball St. College Area](https://images.trvl-media.com/lodging/1000000/440000/439900/439869/e5bfc26e_y.jpg) ### Super 8 by Wyndham Muncie/Ball St. College Area 10/10 Excellent "Very nice stay clean room and great location very quiet and parking for a 53' " [](https://expedia.com/Muncie-Hotels-Super-8-By-Wyndham-MuncieBall-St-College-Area.h439869.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 "Friendly staff, easy check in " [](https://expedia.com/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ![Home2 Suites By Hilton Muncie](https://images.trvl-media.com/lodging/118000000/117740000/117733400/117733348/0ce9f64a_y.jpg) ### Home2 Suites By Hilton Muncie 10/10 Excellent "Staff members are excellent and so attentive. They know me by name and can't do enough for me! I highly recommend!" [](https://expedia.com/Muncie-Hotels-Home2-Suites-By-Hilton-Muncie.h117733348.Hotel-Information) ![Holiday Inn Express Hotel & Suites Greenville by IHG](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/a0d3d74c_y.jpg) ### Holiday Inn Express Hotel & Suites Greenville by IHG 10/10 Excellent "Clean room " [](https://expedia.com/Sidney-Hotels-Holiday-Inn-Express-Hotel-Suites-Greenville.h861235.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | | | ----------------- | ---------- | | Accommodation | 8 Cottages | | Lowest Price | $323 | | Highest Price | $323 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Historic Shopping & Dining District of Winchester ](https://www.expedia.com/Historic-Shopping-Dining-District-Of-Winchester-Hotels.0-l553248621532658844-0.Travel-Guide-Filter-Hotels) - [Hotels near Randolph County Courthouse ](https://www.expedia.com/Randolph-County-Courthouse-Hotels.0-l553248621582419856-0.Travel-Guide-Filter-Hotels) - 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