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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/c2b53613.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) ![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/115000000/114450000/114449900/114449821/1656a0b2.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) ### 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) ![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/a9129cab.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) ![Private kitchen](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/3fbb6c0f.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 4 - Mar 5 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) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/434d3589.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) "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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&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) ![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) ![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) ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg) ### The Campbell House Lexington, Curio Collection by Hilton 10/10 Excellent "Met expectations in every way. Personable and focused on ensuring excellence from the room accommodations to the Rackhouse Tavern serving staff. Tell Stefan we say “Hello and well done!” Outstanding value. Appreciated quality." [](https://expedia.com/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Wonderful time…" [](https://expedia.com/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.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 - 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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