Title: Winchester, IN Cottage Rentals from $218 | 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 27 - Mar 29](https://www.expedia.com/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) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6046207&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 three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6046207&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) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6046207&startDate=2026-07-03&endDate=2026-07-05&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/125000000/124960000/124955500/124955411/3557a186.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) ### 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 $297 nightly $329 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Economy-Hotels-Pets-Welcome-Quiet-Economy-Home-W-Spacious-Yard.h124955411.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91270000/91262400/91262375/8041c624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Paper towels](https://images.trvl-media.com/lodging/92000000/91270000/91262400/91262375/c05b1ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91270000/91262400/91262375/73cf3299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91270000/91262400/91262375/1e022470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaker Hill Cottage on gated estate with fire pit & hiking trails [](https://www.expedia.com/Richmond-Hotels-Quaker-Hill-Cottage-On-Gated-Estate-With-Fire-Pit-Hiking-Trails.h91262375.Hotel-Information) Richmond 9.6/10 Exceptional (30 reviews) "Very easy to find and such a charming home! Very quiet and beautiful area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie P. $195 nightly $218 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Richmond-Hotels-Quaker-Hill-Cottage-On-Gated-Estate-With-Fire-Pit-Hiking-Trails.h91262375.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=2026-03-30&endDate=2026-03-31®ionId=6046207&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style 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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME) 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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CABIN) 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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&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 ![Fairfield Inn by Marriott Muncie](https://images.trvl-media.com/lodging/1000000/20000/14300/14243/9762721b_y.jpg) ### Fairfield Inn by Marriott Muncie 8/10 Good "The room was clean and not too much noise since it was right next to the road. For the price I gave it a good because it was out dated." [](https://expedia.com/Muncie-Hotels-Fairfield-Inn-By-Marriott-Muncie.h14243.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 8/10 Good "Hotel was pretty clean, pool was warm and the room did its job. Nothing special, but a safe place to spend the night" [](https://expedia.com/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.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 "Excellent " [](https://expedia.com/Muncie-Hotels-Home2-Suites-By-Hilton-Muncie.h117733348.Hotel-Information) ![Courtyard Muncie at Horizon Convention Center](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/79a5f4d6_y.jpg) ### Courtyard Muncie at Horizon Convention Center 8/10 Good "The rooms could use a little updating they were clean. The lighting could be improved in the rooms. It was hard to see to do some work. The bed was very good. Pillows were good was a little surprised about how much it cost to get breakfast whereas the Hampton Inn I just stayed at was complementary." [](https://expedia.com/Muncie-Hotels-Courtyard-Muncie-At-Horizon-Convention-Center.h12755848.Hotel-Information) ![Motel 6 Richmond, IN](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/7046bbba_y.jpg) ### Motel 6 Richmond, IN 10/10 Excellent "Our room was clean. Staff was friendly. The hallways needed cleaning. Overall, good stay." [](https://expedia.com/Richmond-Hotels-Motel-6-Richmond.h50102.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 8/10 Good "We were pretty upset that the pool was under maintenance. When I booked the hotel there was no mention of it." [](https://expedia.com/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) ![Muncie Place Hotel & Suites](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/e0a75b6c_y.jpg) ### Muncie Place Hotel & Suites 4/10 Poor "They didn’t have breakfast for us that time.. The pool been closed through the weekend. " [](https://expedia.com/Muncie-Hotels-Holiday-Inn-Express-Hotel-Suites-Muncie.h67438.Hotel-Information) ![Comfort Suites Richmond East](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/c84ecc16_y.jpg) ### Comfort Suites Richmond East 10/10 Excellent "Breakfast was excellent. The person in charge went the extra mile to make sure everything was properly prepared." [](https://expedia.com/Richmond-Hotels-Comfort-Suites.h92418479.Hotel-Information) ![Best Western Plus Richmond Indiana I-70](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/8a818798_y.jpg) ### Best Western Plus Richmond Indiana I-70 10/10 Excellent "Clean room. Spacious. Great breakfast. I enjoyed the Belgium waffel." [](https://expedia.com/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | | | ----------------- | ---------- | | Accommodation | 8 Cottages | | Lowest Price | $218 | | Highest Price | $329 | ## 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) - [Hotels near Winchester Golf Club ](https://www.expedia.com/Winchester-Golf-Club-Hotels.0-l553248621582419855-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Speedway ](https://www.expedia.com/Winchester-Speedway-Hotels.0-l6289044-0.Travel-Guide-Filter-Hotels) - 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