Title: Winchester B&B: Find the Best Bed and Breakfast from CA $345 | 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 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Building design](https://images.trvl-media.com/lodging/1000000/920000/911400/911310/a33e3a46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/920000/911400/911310/2b217cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/920000/911400/911310/af2dcba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911310/0f0f54b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chez Lyndon Manor [](https://www.expedia.ca/Lexington-Hotels-Lyndon-House-BB.h911310.Hotel-Information) Northside District 9.6/10 Exceptional (123 reviews) "Great breakfast!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill CA $288 CA $345 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Lexington-Hotels-Lyndon-House-BB.h911310.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=2026-04-18&endDate=2026-04-19®ionId=7876&adults=2&lodging=BED_AND_BREAKFAST&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-Bed-And-Breakfast.d7876-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d7876-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "This place is awesome. So much character." [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.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 8/10 Good "Clean hotel and nice staff " [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.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 2/10 Terrible "Went to wash hands and was out of hand soap on the wall. In the shower there was an extra bottle of body wash sitting on the tub edge that I assume the guest prior to us asked for since the one on the wall was empty so I used that. When I went to take shower the next day, the body wash bottle on the wall was empty which is why there was that extra bottle sitting on the tub edge. That tells me the room must not have been cleaned from previous guest or housekeeping would’ve put that bottle on the wall to replace the empty one! Then in the middle of the shower I went to use the shampoo on the wall, and it was empty too!!!! Thank God I wasn’t alone and could send husband down to get me a bottle to use! It’s a shame that just the expected amenities were not checked and filled or changed out! Was our room cleaned from prior guest???? That’s questionable! I think just the beds were done & that's that! Then very early morning when it was still dark we kept hearing lots of loud noises and booms in hallway and below us. There was a function that was going to be going on the next day and I guess they were getting things moved and ready and delivered for that. It kept us from sleeping It was awful stay! " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/31fbd799_y.jpg) ### Hilton Lexington/Downtown 8/10 Good "Yes" [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.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 6/10 Okay "Our a/c in our room didn’t work and the room was 77 degrees super hot. We called down to the front desk around 11pm when we got back from swimming and they said they’d send someone up. We waited 30-45 min and no one showed so had to call again and they apologized and said they’d try to get someone up. We were so tired from our day traveling. Or kids were super tired but couldn’t sleep in the heat. They sent maintenance up and he worked on it for a bit and told us to check about another room. They were able to get us another room on the same floor so we went and same thing. A/C wasn’t working. The maintenance guy said they just had someone there to work on the a/c so something must of happened. Finally about 12:30 we hopped to our 3rd room on a different floor and that a/c worked. The hotel didn’t give us any sort of discount with all the hassle we went through. Poor customer service. The hot tub was also cautioned off so we weren’t able to use that either." [](https://expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.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 10/10 Excellent "Great place. The staff were very friendly & very accommodating! I threw in a last minute request and they went out of their way to help and had things taken care of immediately! The property is beautiful and very well maintained! We visited 3 other places in the area & had the same experience at all of them! Hidden gems all of them! " [](https://expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](https://images.trvl-media.com/lodging/1000000/210000/203600/203587/54c27b3e_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "Staff was very friendly and helpful. Room was exceptionally clean. Breakfast was very good, good selections. Convenient to attractions. Parking was easy. Would stay here again happily." [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/0b8cf614_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Staff was very friendly. Rooms were large and clean. Beds were super comfy. Great stay at a good price!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/e4c398a8_y.jpg) ### The Manchester 10/10 Excellent "lovely additional activities. loved yoga on sunday" [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 123 | | ----------------- | ------- | | Accommodation | 5 B&B | | Lowest Price | CA $345 | | Highest Price | CA $345 | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### How do you know if a B&B is a good option for you? ### What are the best B&Bs in Winchester? ### When is the best time to book my B&B in Winchester? ### What is there to do in Winchester? ### How can I get to and around Winchester? ## 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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