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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=7876&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.com/Hotel-Search?regionId=7876&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.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 four 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) ## Our top choices for Winchester cottages ![Exterior](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/2afdae23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/a67e8575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/d2416d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/b2ad1a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountaintop Cottage [](https://www.expedia.com/Stanton-Hotels-Mountaintop-Cottage.h108513805.Hotel-Information) Stanton 10/10 Exceptional (27 reviews) "I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica H. $175 nightly $193 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Stanton-Hotels-Mountaintop-Cottage.h108513805.Hotel-Information) ![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/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) ![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) ### 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 Feb 16 - Feb 17 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) ![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/a9129cab.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 Mar 1 - Mar 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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/5e270a80.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) ### 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) "The house and Host were perfect! We had such a great weekend. And the house was the perfect home away from home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melinda F. $617 nightly $716 total Feb 15 - Feb 16 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=2026-02-28&endDate=2026-03-01®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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE) 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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APARTMENT) 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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CONDO) 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=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&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 ![Everhome Suites Lexington - Horse Park](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/89ad308c_y.jpg) ### Everhome Suites Lexington - Horse Park 10/10 Excellent "Friendly front staff, very clean, and set at a good location. " [](https://expedia.com/Lexington-Hotels-Everhome-Suites-Lexington-North.h101171857.Hotel-Information) ![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/7f6a345c_y.jpg) ### 21c Museum Hotel Lexington 10/10 Excellent "The room was large, the staff were helpful, the hotel was well located." [](https://expedia.com/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "Friendly and attentive staff. Great location, bar and onsite restaurant. " [](https://expedia.com/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/2dacd96b_y.jpg) ### Country Inn & Suites by Radisson, Georgetown, KY 10/10 Excellent "Staff was very friendly and courteous. Rooms very clean. Highly recommend" [](https://expedia.com/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Room was great! Staff was awesome. Being able to go into Rupp without going outside, the best. " [](https://expedia.com/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "This was the cleanest hotel I have stay at and that’s saying a lot considering how much ch I travel. No the breakfast isn’t eggs bacon ect. But you won’t be disappointed. Cereal bagels toast juice coffee. If that’s not for you fine but stop dinging them for breakfast. " [](https://expedia.com/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "clean room, nice pool, Good breakfast " [](https://expedia.com/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Fairfield Inn & Suites by Marriott Lexington North](https://images.trvl-media.com/lodging/3000000/2810000/2803700/2803646/6ec64b2f_y.jpg) ### Fairfield Inn & Suites by Marriott Lexington North 10/10 Excellent "Room was great, staff was great, " [](https://expedia.com/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg) ### DoubleTree Suites by Hilton Hotel Lexington 10/10 Excellent "All of the above " [](https://expedia.com/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | 53 | | ----------------- | ----------- | | Accommodation | 34 Cottages | | Lowest Price | $146 | | Highest Price | $716 | ## 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 - 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