Title: Winchester Cottages from CA $326 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hyelsinta # Search Winchester Cottage Rentals from CA $326 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select 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/aedf86bd.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/f447e693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre Frenchburg 10/10 Exceptional (1) "The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! " CA $151 CA $326 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Frenchburg-Hotels-Peaceful-Frenchburg-Cabin-W-Private-Hot-Tub.h114449821.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/d2416d0d.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) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/b2ad1a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/ad0d3e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountaintop Cottage Stanton 10/10 Exceptional (18) "The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions." CA $188 CA $269 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Stanton-Hotels-Mountaintop-Cottage.h108513805.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) ![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81252100/81252089/a9129cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique, Cozy Stay near Red River Gorge Slade 7.4/10 Good (9) "Me and my girlfriend had a great time enjoy the area around were we were staying and had a great time and the people their were nice" CA $108 CA $203 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Slade-Hotels-Unique.h81252089.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70270000/70262600/70262582/cb7c7f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk](https://images.trvl-media.com/lodging/71000000/70270000/70262600/70262582/d081bccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70270000/70262600/70262582/80523cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/71000000/70270000/70262600/70262582/e09c4daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bungalow | 1 Bed, 0.5 Bath Stanton 9.6/10 Exceptional (5) "If you're looking for an off grid sleeping porch in the red river gorge, this one has a nice wooded view." CA $151 CA $279 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Stanton-Hotels-Bungalow-1-Bed.h70262582.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93230000/93222000/93221957/864e97ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93230000/93222000/93221957/185b84ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93230000/93222000/93221957/8e8085ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/94000000/93230000/93222000/93221957/11ab94aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Springside BoHo Getaway Georgetown 9.8/10 Exceptional (50) "Jonathon provided a great stay. " CA $209 CA $428 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Lexington-Hotels-Springside-BoHo-Getaway.h93221957.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/4df76530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/8f803a84.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) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92180000/92178500/92178452/a565c287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Perfect for Girls Night Away Lexington 10/10 Exceptional (11) "This place is just charming. We were in town for our daughter’s graduation from UK and your place was perfect. Spacious and so comfy. " CA $557 CA $1,015 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21®ionId=7876&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d7876-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d7876-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Motel 6 Lexington, KY - East I-75](//images.trvl-media.com/lodging/2000000/1040000/1039800/1039703/c1f9e9cf_y.jpg) ### Motel 6 Lexington, KY - East I-75 10/10 Excellent "Resturants and walmart close by " [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h1039703.Hotel-Information) ![Tru by Hilton University Medical Center](//images.trvl-media.com/lodging/79000000/78010000/78004900/78004839/9823f52b_y.jpg) ### Tru by Hilton University Medical Center 10/10 Excellent "The staff was readily available and the hotel met all expectations" [](https://expedia.ca/Lexington-Hotels-Tru-By-Hilton-Lexington-University-Medical-Center.h78004839.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](//images.trvl-media.com/lodging/1000000/290000/283200/283165/60f6cd78_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Wonderful experience and my dog loved every minute " [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Spark by Hilton Lexington Hamburg](//images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Staff was very friendly and helpful. Room was clean." [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Clean room and friendly staff" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![GLō Best Western Lexington](//images.trvl-media.com/lodging/1000000/130000/123900/123895/c0739f84_y.jpg) ### GLō Best Western Lexington 10/10 Excellent "Staff was very accommodating." [](https://expedia.ca/Lexington-Hotels-GLo-Best-Western-Lexington.h123895.Hotel-Information) ![Origin Lexington a Wyndham Hotel](//images.trvl-media.com/lodging/34000000/33800000/33790700/33790682/7bb47690_y.jpg) ### Origin Lexington a Wyndham Hotel 10/10 Excellent "Very clean and the staff was very friendly. Will stay at property again. " [](https://expedia.ca/Lexington-Hotels-Origin-Hotel-Lexington.h33790682.Hotel-Information) ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Clean room" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![The Manchester ](//images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "Very fancy, clean, fun" [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | 1 | | --- | --- | | Accommodation | 35 Cottages | | Lowest Price | CA $326 | | Highest Price | CA $326 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Applebee s Park](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - 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