Title: Winchester Guest Houses from CA $231 | 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) ![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/7876/276db1f8-3da6-41f2-8d63-03ef378c3f6b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7876/276db1f8-3da6-41f2-8d63-03ef378c3f6b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Dining](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/027f1b3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/755ab65f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/20aa5388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/4b9ff374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury on Main / North [](https://www.expedia.ca/Lexington-Hotels-Luxury-On-Main-North.h37611132.Hotel-Information) Richmond 9.8/10 Exceptional (104 reviews) "Nicely , well done vintage brick house - easy access and comfortable .I highly recommend staying here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan S. CA $114 CA $231 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Lexington-Hotels-Luxury-On-Main-North.h37611132.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=2026-04-07&endDate=2026-04-08®ionId=7876&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d7876-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d7876-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![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 "." [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.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 "My room was clean. The property was clean and new looking. I liked how the lobby is decorated and looks clean." [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/8e22f4aa_y.jpg) ### Hyatt Regency Lexington 2/10 Terrible "Waited 2.5 hrs after check in time for room, was late to the concert due to this." [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Natural Bridge State Resort Park](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/324d2660_y.jpg) ### Natural Bridge State Resort Park 8/10 Good "It was the best property in the area to stay at. If you can get a room, take it. " [](https://expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/31fbd799_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Check in was easy loved getting a text message personally from the front desk keeping up asking me if I needed anything. I’m giving me the text number personally if I needed something from them will definitely be there again." [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "The room was elegant and roomy, filled with light and added touches like real plants and marble window sills. The shower was amazing. The toiletries were lovely. And they put out coffee in the lobby at 7:00." [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/e4c398a8_y.jpg) ### The Manchester 8/10 Good "Hotel and room was beautiful. Upscale without being snooty. Very clean. Check in staff were just okay. No water or anything offered. No ice on any floor and had to go down to bar for a glass of ice. Mini fridge is so packed w hotel beverages for purchase there is no room for your own. No iron/board in room. There is a hotel shuttle to downtown events. No one mentioned that but it passed as we were walking to our event. " [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.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 6/10 Okay "We got a king room and pillows were the size of a toddlers bed? I could barely sleep due to lack of head space lol. Also upset that there was no potatoes for the breakfast. Otherwise the hotel was fine. " [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.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 room was clean and the staff was very friendly…. The convenience of have the Bistro downstairs was super. The food was great. Definitely will stay again next year when in town." [](https://expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 104 | | ----------------- | -------------- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $231 | | Highest Price | CA $231 | ## Frequently asked questions ### What are the most popular guest houses in Winchester according to reviews? ### What is the nightly rate for a guest house in Winchester? ### What's the difference between a Winchester guest house and a B&B? ## 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) - [Motels in Camargo ](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Chevy Chase ](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Beach-Hotel.0-n553248635976481361-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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