Title: Winchester, KY Cottage Rentals from $146 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx7876)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d7876.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d7876.Destination-Travel-Guides) ![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.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=7876&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=7876&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=7876&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=7876&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/115000000/114450000/114449900/114449821/93d4b238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/82087122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/c80904f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/618a1df1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre [](https://www.expedia.com/Frenchburg-Hotels-Peaceful-Frenchburg-Cabin-W-Private-Hot-Tub.h114449821.Hotel-Information) Frenchburg 10/10 Exceptional (2 reviews) "The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler $236 nightly $262 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Frenchburg-Hotels-Peaceful-Frenchburg-Cabin-W-Private-Hot-Tub.h114449821.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/d92edf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/3fbb6c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/7b07795c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/7098069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique, Cozy Stay near Red River Gorge [](https://www.expedia.com/Slade-Hotels-Unique.h81252089.Hotel-Information) Slade 7.4/10 Good (10 reviews) "Great for a quick one nite stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khanrad W. $133 nightly $146 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Slade-Hotels-Unique.h81252089.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/1c77aa3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/ab6c98d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/5e270a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/add87bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Perfect for Girls Night Away [](https://www.expedia.com/Lexington-Hotels-The-Lady-Clay-A-Pink-Cottage-In-Lexington.h92178452.Hotel-Information) Lexington 10/10 Exceptional (14 reviews) "This house is just as cute as the pictures with enough space for a large group. It’s also located within walking distance to good dining and shopping!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monica W. $662 nightly $768 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Lexington-Hotels-The-Lady-Clay-A-Pink-Cottage-In-Lexington.h92178452.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=2026-03-26&endDate=2026-03-27®ionId=7876&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_7876) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CHALET) ![](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.d7876-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d7876-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/db3edf18_y.jpg) ### Country Inn & Suites by Radisson, Georgetown, KY 10/10 Excellent "The room was clean and spacious, and the staff was very accommodating." [](https://expedia.com/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![Holiday Inn Express Lexington Horse Park Area by IHG](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/b7d6b7de_y.jpg) ### Holiday Inn Express Lexington Horse Park Area by IHG 10/10 Excellent "Everything was fine. " [](https://expedia.com/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) ![Marriott Lexington Griffin Gate Golf Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef_y.jpg) ### Marriott Lexington Griffin Gate Golf Resort & Spa 10/10 Excellent "The hotel was very clean and relaxing. " [](https://expedia.com/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) ![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/973ee071_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Room was clean and well maintained. The pool was clean and well kept too. " [](https://expedia.com/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/653cb913_y.jpg) ### 21c Museum Hotel Lexington 10/10 Excellent "The rooms are nice. Location is great! We have stayed at many different hotels in Lexington. This one is one of my favorites. It’s quiet at night (I think Lexington can be a little loud with cars at night) but these rooms are very quiet. The art exhibit is great bonus and fun to explore. Would highly recommend" [](https://expedia.com/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/8e22f4aa_y.jpg) ### Hyatt Regency Lexington 8/10 Good "Rooms are aged and basic. Breakfast was good" [](https://expedia.com/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/e4c398a8_y.jpg) ### The Manchester 10/10 Excellent "We were upgraded to a corner double queen suite. The staff is always wonderful. Very convenient walk to Manchester Music Hall next door. " [](https://expedia.com/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 4/10 Poor "Staff was wonderful. Room very clean. Bed and pillows was very uncomfortable, that is my only complaint " [](https://expedia.com/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Motel 6 Lexington, KY - Airport](https://images.trvl-media.com/lodging/1000000/20000/18500/18423/c6ac75fa_y.jpg) ### Motel 6 Lexington, KY - Airport 10/10 Excellent "Staff is amazing" [](https://expedia.com/Lexington-Hotels-Motel-6-Lexington.h18423.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | 16 | | ----------------- | ----------- | | Accommodation | 34 Cottages | | Lowest Price | $146 | | Highest Price | $768 | ## Frequently asked questions ### Why book your cottage in Winchester with Expedia? ### How can I find cheap cottages in Winchester? ### What is there to do in Winchester near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Bluegrass Heritage Museum ](https://www.expedia.com/Bluegrass-Heritage-Museum-Hotels.0-l553248621561880736-0.Travel-Guide-Filter-Hotels) - 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