Title: Winchester Condo Rentals from CA $281 | 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 Condos Rentals in Winchester from CA $281 ![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 Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Condo Rentals ## Our top choices for Winchester condo rentals ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034706/3be87d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034706/e7dc5eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034706/e34eb93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034706/82cd3778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Walkable Downtown - Rupp Arena - Keeneland Downtown Lexington 7.2/10 Good (5) "Positive place" CA $151 CA $281 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Lexington-Hotels-506-175-LEXWalk-To-Rupp-Arena.h91034706.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/4bc6098a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/8e089dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/514670aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/f7a1694e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Stunning Downtown Views on Main Street! Downtown Lexington 9.8/10 Exceptional (40) "Very clean and convenient to Rupp arena " CA $164 CA $298 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Lexington-Hotels-508-175-LEX-Walk-Downtown-Rupp-Arena.h91075048.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112980000/112971100/112971080/b942f123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/113000000/112980000/112971100/112971080/c3fbb693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112980000/112971100/112971080/c18f76bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112980000/112971100/112971080/eb5b8baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom family friendly condo conveniently located near downtown Lexington Lexington 8.0/10 Very good (1) "The condo worked perfect for us as we went to baseball games at UK. Location was great. Acess to restaurants and coffee shops was great! " CA $256 CA $563 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Lexington-Hotels-3-Bedroom-Family-Friendly-Condo-Conveniently-Located-Near-Downtown-Lexington.h112971080.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034698/f68d8793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034698/99cd82ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034698/77656425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034698/2ded4964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Walkable Downtown Condo - Stunning View Downtown Lexington 9.6/10 Exceptional (8) "Great stay" CA $159 CA $291 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-501-175-LEXWalk-To-Rupp-Arena.h91034698.Hotel-Information) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91020000/91010200/91010163/490bb6d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/92000000/91020000/91010200/91010163/f19cf33b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91020000/91010200/91010163/4708a808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91010200/91010163/04c13aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Spacious Two Bedroom! Walkable Downtown! Downtown Lexington 9.0/10 Wonderful (10) "Great place to stay for a weekend, had everything we needed and convenient location." CA $173 CA $336 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Lexington-Hotels-504-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010163.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/e3e0d238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/090a7767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/7fe326c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/e4bb3cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Loft in Downtown Lexington, Rupp Arena Downtown Lexington 10/10 Exceptional (1) "We had a great stay! The location was perfect for downtown and within easy walking distance from attraction and Target market. Very clean and easy access!" CA $159 CA $291 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Lexington-Hotels-503-175LEXWalk-To-Rupp-Arena.h91034704.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91020000/91010900/91010891/a0490dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010900/91010891/e795ac77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010900/91010891/575d6907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010900/91010891/cd39c887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Two Bedroom Condo, Walkable Downtown! Downtown Lexington 9.8/10 Exceptional (11) "Great stay!" CA $173 CA $339 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Lexington-Hotels-604-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010891.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74120000/74114400/74114349/fc2f5536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74120000/74114400/74114349/72fee52e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/75000000/74120000/74114400/74114349/bc4623cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74120000/74114400/74114349/w1439h1550x1y1-4a9d2e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graffiti Art Haus - Walk to Central Bank Arena Downtown Lexington 10/10 Exceptional (34) "Perfect place to stay for visiting downtown Lexington. " CA $122 CA $298 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Lexington-Hotels-Cool-Condo-2-Blocks-To-Rupp-Distillery-District.h74114349.Hotel-Information) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/f6100ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/15a5e93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/388da7e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/c68d03de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY. Lexington 8.8/10 Excellent (8) "We enjoyed our girls weekend and this place was perfect !" CA $173 CA $286 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Lexington-Hotels-This-Condominium-Is-A-1-Bedroom.h96239461.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96540000/96530600/96530516/285012c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96540000/96530600/96530516/64a804e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/97000000/96540000/96530600/96530516/cc479f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96540000/96530600/96530516/9bc2f44c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Spacious Two Bedroom - Near Rupp Arena! Downtown Lexington 9.6/10 Exceptional (15) "Great location, easy access to all things downtown" CA $173 CA $336 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Spacious-Two-Bedroom-Near-Rupp-Arena.h96530516.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97010000/97001000/97000993/e19ec22a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/98000000/97010000/97001000/97000993/3df15e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97010000/97001000/97000993/w1324h900x0y0-f4ead31c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/98000000/97010000/97001000/97000993/0b3b924d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gatsby Getaway, Downtown LEX Downtown Lexington 10/10 Exceptional (15) "Comfortable room and great downtown location." CA $173 CA $308 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Lexington-Hotels-The-Gatsby-Getaway-Quiet-Condo-Hotel-On-Main-St-Walkable-Downtown-Lexington.h97000993.Hotel-Information) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/103000000/102070000/102065400/102065366/29ddef1b.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/103000000/102070000/102065400/102065366/b829e88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/103000000/102070000/102065400/102065366/46698a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102070000/102065400/102065366/9985b2eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lex In The City - Downtown Condo Downtown Lexington 9.8/10 Exceptional (7) "The place was great. Good location downtown. The bed was one of the most comfortable I have had at a rental space. " CA $159 CA $291 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-Lex-In-The-City-Downtown-Condo.h102065366.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/8df2312e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/cd788f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/ec1d548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/5e9871bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Quiet Loft Near Rupp Arena & Restaurants Downtown Lexington 10/10 Exceptional (1) "Very convenient apartment in downtown Lexington. Loved being able to walk to the great restaurants nearby and to visit our student at the University of Kentucky." CA $159 CA $292 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-502-175-LEXWalk-To-Rupp-Arena.h91010326.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102653100/102653067/cbdf32f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102653100/102653067/654d8fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102660000/102653100/102653067/4bd18dfa.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/103000000/102660000/102653100/102653067/49b99565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Lex Full Friends Condo Downtown Lexington 9.0/10 Wonderful (2) "Overall, the condo was clean, spacious, and well-maintained. Security was exceptional with key codes needed for doors and elevator. Felt safe in the downtown urban setting. Enjoyed our two-night stay but noise from the central heating unit interrupted our sleep. The TV and Wi-Fi worked great and problem-free, and the electronic fireplace was a nice touch. Parking can be tricky and is not on-site but we managed to find free street parking thanks to the holiday hours" CA $173 CA $314 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Lexington-Hotels-Downtown-Lex-Full-Friends-Condo.h102653067.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/115000000/114760000/114758200/114758162/11770baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114760000/114758200/114758162/76ad650b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114760000/114758200/114758162/62563f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114760000/114758200/114758162/ecfe3735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Retreat- a perfect-sized condo for your Bourbon Trail adventure Downtown Lexington 10/10 Exceptional (1) [](https://www.expedia.ca/Lexington-Hotels-The-Retreat-A-Perfect-Sized-Condo-For-Your-Bourbon-Trail-Adventure.h114758162.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/d9d56065.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/db9608c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bourbon Condo Downtown Lexington Downtown Lexington 10/10 Exceptional (11) "Perfect location, clean and great place to stay. Will stay here again next time we attend an event." CA $173 CA $336 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/ff8f51eb.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) ![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) ![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 Downtown Lexington 9.4/10 Exceptional (3) "Beautifully appointed condo, amazingly quiet, given downtown location. Excellent communication with owner. No parking on-site, so you have to find parking in nearby garages, very limited street parking. Convenient location, would definitely stay again." CA $151 CA $282 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/e8cf9444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/f2ffe733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/cf46ae0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/3e035c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Spacious Two Bedroom Downtown Lexington Downtown Lexington 9.6/10 Exceptional (30) "Claire was wonderful to work with" CA $187 CA $365 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Lexington-Hotels-507-175-LEXWalk-To-Rupp-Arena.h91034708.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102680000/102672100/102672011/20c6e207.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/103000000/102680000/102672100/102672011/63dfad99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102680000/102672100/102672011/6c83c18b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102680000/102672100/102672011/3481aa8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown LEX - Keeneland Condo Downtown Lexington 8.0/10 Very good (3) "Great accommodations !!Stayed for one night dropping my daughter off for her fall semester at UK.Convenient to downtown restaurants !" CA $151 CA $281 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Lexington-Hotels-Downtown-LEX-Keeneland-Condo.h102672011.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/36000000/35100000/35092200/35092128/86a63dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35100000/35092200/35092128/28874e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35100000/35092200/35092128/cb07756b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35100000/35092200/35092128/7bde6668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown Downtown Lexington 10/10 Exceptional (78) "Wonderful condo in fun location, great parking, comfy beds, helpful Hosts!" [](https://www.expedia.ca/Lexington-Hotels-Paradiso-Divine-Condo.h35092128.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=2025-10-08&endDate=2025-10-09®ionId=7876&adults=2&lodging=CONDO&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-Condos.d7876-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Condos.d7876-aaCondos.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Hyatt Place Lexington](//images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "Everyone was very friendly. The customer service was great too. Breakfast was ok. The kids loved the pool" [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Lexington](//images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg) ### DoubleTree Suites by Hilton Hotel Lexington 10/10 Excellent "I like the room" [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.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 "The first night we were there the toilet unfortunately broke. They moved us immediately and helped us move. The very last day we were there, a rains tome came through and we saw that the window was leaking from the top. They offered to move us again, however we decline as we were leaving less than 12 hours later. Overall 10/10" [](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 "We loved our stay at thos property. The staff was very friendly and the hotel was very clean. " [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Holiday Inn Lexington - Hamburg by IHG](//images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/776ae294_y.jpg) ### Holiday Inn Lexington - Hamburg by IHG 10/10 Excellent "Japanese Restaurant on the premises. Very friendly hotel staff." [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.Hotel-Information) ![Best Western Winchester Hotel](//images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1_y.jpg) ### Best Western Winchester Hotel 10/10 Excellent "Older establishment Clean, very quiet, lovely fresh breakfast. 100% will return " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.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 "Love the place " [](https://expedia.ca/Lexington-Hotels-GLo-Best-Western-Lexington.h123895.Hotel-Information) ![The Manchester ](//images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "One of the best boutique hotels I’ve stayed at" [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "I loved everything about the Elwood Hotel. Cleanliness, security, beds!!!! I will definitely stay there again! " [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 267 | | --- | --- | | Accommodation | 58 Condo Rentals | | Lowest Price | CA $281 | | Highest Price | CA $563 | ## 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) - [Golf Hotels in Chevy Chase](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Golf-Hotel.0-n553248635976481361-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Chevy Chase](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976481361-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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