Title: Book the Best HISTORIC Hotels in Winchester in 2026 | 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 availability on Winchester Historic Hotels Tonight [Mar 28 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-28&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 29 - Mar 30](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-29&endDate=2026-03-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-03&endDate=2026-04-05&adults=2&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester historic hotels ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/a5d982e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/2be214c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/3f402f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/a160cec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique Stay in a 1907 Log Cabin on The Kentucky River [](https://www.expedia.ca/Lexington-Hotels-Unique-Stay-In-A-1907-Log-Cabin-On-The-Kentucky-River.h44774926.Hotel-Information) Lexington 9.6/10 Exceptional (108 reviews) "This is a unique property, it feels like stepping into history. It is well maintained, clean and comfortable but not your average stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennie C. CA $132 CA $249 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lexington-Hotels-Unique-Stay-In-A-1907-Log-Cabin-On-The-Kentucky-River.h44774926.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/2078de17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/e9dba827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/6372f5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/1bae486e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Suite-🕊️ at Bleubird Studio, In-Suite Bath, 5-Star Stay [](https://www.expedia.ca/Lexington-Hotels-East-Suite-Bleubird-Studio-Suites-Art-Gallery-Yoga-Boutique-Stay.h38198837.Hotel-Information) Georgetown 10/10 Exceptional (61 reviews) "Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) l v. CA $173 CA $321 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lexington-Hotels-East-Suite-Bleubird-Studio-Suites-Art-Gallery-Yoga-Boutique-Stay.h38198837.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/bbfb6def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/50928ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/68ae97c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/2bbaa45c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Kentucky Horse Country [](https://www.expedia.ca/Paris-Hotels-Cabin-In-Kentucky-Horse-Country.h26955325.Hotel-Information) Bourbon County 10/10 Exceptional (81 reviews) "The cabin was unique if only for its location on the farm. It was as secure as we could have asked for. A definite gem. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vickie B. CA $452 CA $676 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Paris-Hotels-Cabin-In-Kentucky-Horse-Country.h26955325.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/37dc7dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/db9608c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/w1324h900x25y0-a508f784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/3f48eff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bourbon Condo Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.Hotel-Information) Downtown Lexington 10/10 Exceptional (12 reviews) "Great stay and very clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan L. CA $191 CA $373 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/2e346aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/190d3861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/ed30953c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/af0f2410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location [](https://www.expedia.ca/Lexington-Hotels-Morrison-Cabin-Offers-The-Finest-Interiors.h33642557.Hotel-Information) Downtown Lexington 10/10 Exceptional (150 reviews) "Good location and plenty of room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol W. CA $368 CA $660 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Lexington-Hotels-Morrison-Cabin-Offers-The-Finest-Interiors.h33642557.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/52b1d9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/9032a361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/17cea644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/8de63351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet Downtown Lexington Bougie Apartment [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information) Downtown Lexington 9.6/10 Exceptional (4 reviews) "Great location in downtown Lexington! The place was clean and well appointed. We would definitely rent again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bernadette R. CA $160 CA $296 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/e0e7ce75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/29f4dcb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/ed8c69b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/552aa482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms [](https://www.expedia.ca/Lexington-Hotels-Lafferty-House-Walk-To-UK.h34088471.Hotel-Information) Downtown Lexington 10/10 Exceptional (53 reviews) "Great Stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $402 CA $687 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Lexington-Hotels-Lafferty-House-Walk-To-UK.h34088471.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=2026-04-11&endDate=2026-04-12®ionId=7876&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/db3edf18_y.jpg) ### Country Inn & Suites by Radisson, Georgetown, KY 6/10 Okay "I was there for test so I was unable to eat. My nephew enjoyed it" [](https://expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.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 10/10 Excellent "Clean comfortable beds. Staff super nice. " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.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 8/10 Good "We didn’t stay for breakfast. I do have a huge complaint about the shower. The curtain was too short so when you took a shower it let water spill out. It made quite a mess and was a hazard because of the wet floor. The shower faucet looked liked it was ready to fall off." [](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 "Teo thumbs up!!" [](https://expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.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 "Very clean, great location, loved the indoor pool!" [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/68f1f7a4_y.jpg) ### The Campbell House Lexington, Curio Collection by Hilton 8/10 Good "Room was clean but bathroom could use a counter food was great salmon was perfectly cook the quail was cook well we enjoyed the music while we ate over all was very happy with our stay " [](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![Motel 6 Lexington, KY - Airport](https://images.trvl-media.com/lodging/1000000/20000/18500/18423/c6ac75fa_y.jpg) ### Motel 6 Lexington, KY - Airport 10/10 Excellent "Convenient location kinda sketchy at night in the back wish some of the rooms on the front were available seems like they were renovating some areas great service for check in and out can’t remember her name but she was absolutely amazing!" [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h18423.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Nice hotel in convenient location. Easy parking. Staff was friendly and bar looked nice. Room was very large with lots of space. Quick trip with my daughter and this was perfect spot to visit University of Kentucky. Would recommend " [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/8e22f4aa_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "So convenient to " [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Winchester? ### How many historical hotels are located in Winchester? ### What are the most important historical places and other sights to visit in Winchester? ### What is a historic hotel like in Winchester? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Winchester have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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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