Title: Winchester Condo Rentals from CA $193 | 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) ![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Nawa Aseen # Search Condos Rentals in Winchester from CA $193 - ![](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 In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester condo rentals ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/1f59083d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/1cb7e759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/42c86d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/9dfcb411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-602-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034703.Hotel-Information) 9.8/10 Exceptional (20) "The place was perfect for the weekend. Great location easy to walk to bars, restaurants and the local farmers market. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen R. CA $135 CA $262 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Lexington-Hotels-602-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034703.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) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96540000/96530600/96530516/7ef60987.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Spacious-Two-Bedroom-Near-Rupp-Arena.h96530516.Hotel-Information) 9.6/10 Exceptional (16) "Great location, easy access to all things downtown" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex CA $157 CA $316 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Spacious-Two-Bedroom-Near-Rupp-Arena.h96530516.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) ![TV](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/80a86047.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) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/c68d03de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Lexington [](https://www.expedia.ca/Lexington-Hotels-This-Condominium-Is-A-1-Bedroom.h96239461.Hotel-Information) 9.0/10 Wonderful (10) "We enjoyed our girls weekend and this place was perfect !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison G. CA $130 CA $234 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-This-Condominium-Is-A-1-Bedroom.h96239461.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) ![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) ![Interior](https://images.trvl-media.com/lodging/103000000/102070000/102065400/102065366/3c3441e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-Lex-In-The-City-Downtown-Condo.h102065366.Hotel-Information) 9.8/10 Exceptional (8) "We had a quick visit for my daughter’s graduation. Easy access and good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah S. CA $144 CA $272 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-Lex-In-The-City-Downtown-Condo.h102065366.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105870000/105860200/105860169/c77eb7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105870000/105860200/105860169/4960ae74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105860200/105860169/543c328c.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/106000000/105870000/105860200/105860169/9469da50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Lexington [](https://www.expedia.ca/Lexington-Hotels-Cozy-2-Bedroom-Condo-With-WiFi.h105860169.Hotel-Information) CA $129 CA $385 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Lexington-Hotels-Cozy-2-Bedroom-Condo-With-WiFi.h105860169.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010200/91010163/7ec60d2a.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-504-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010163.Hotel-Information) 9.4/10 Exceptional (14) "Nice little apartment for business travel. Great location - loved the library and Kentucky Theater just across the street. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa J. CA $157 CA $316 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-504-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010163.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/514670aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91080000/91075100/91075048/8d3c4563.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-508-175-LEX-Walk-Downtown-Rupp-Arena.h91075048.Hotel-Information) 9.8/10 Exceptional (44) "Very clean and convenient to Rupp arena " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy R. CA $144 CA $272 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Lexington-Hotels-508-175-LEX-Walk-Downtown-Rupp-Arena.h91075048.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) ![Lobby](https://images.trvl-media.com/lodging/75000000/74120000/74114400/74114349/bc4623cd.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/75000000/74120000/74114400/74114349/w1439h959x1y1-d061dfcf.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-Cool-Condo-2-Blocks-To-Rupp-Distillery-District.h74114349.Hotel-Information) 10/10 Exceptional (36) "Perfect place to stay for visiting downtown Lexington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. CA $108 CA $279 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-Cool-Condo-2-Blocks-To-Rupp-Distillery-District.h74114349.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/c163da2a.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information) 9.6/10 Exceptional (4) "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 $135 CA $262 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.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) ![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) ![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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-Downtown-Lex-Full-Friends-Condo.h102653067.Hotel-Information) 9.0/10 Wonderful (2) "Very clean, nice place, well furnished. Wnjoyed our stay. Convenient downtown location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul B. CA $135 CA $262 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-Downtown-Lex-Full-Friends-Condo.h102653067.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99620000/99610100/99610080/f8b1b58a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99620000/99610100/99610080/a3ec5d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99620000/99610100/99610080/cb567752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99620000/99610100/99610080/a1b219ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Georgetown [](https://www.expedia.ca/Lexington-Hotels-Man-OWar-The-HoMKY-Horse-Park-11minArk-30minWalk-To-Georgetown-College.h99610080.Hotel-Information) 10/10 Exceptional (5) "Very nice place. It fit our needs for a quick stop in Georgetown. Communication with the host was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca M. CA $219 CA $443 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-Man-OWar-The-HoMKY-Horse-Park-11minArk-30minWalk-To-Georgetown-College.h99610080.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/40e581ad_edited_deb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/adcc7b72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/828de569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/5d82b50c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Lexington [](https://www.expedia.ca/Lexington-Hotels-1-Bedroom-Near-The-University-Of-Kentucky.h86007665.Hotel-Information) CA $139 CA $193 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Lexington-Hotels-1-Bedroom-Near-The-University-Of-Kentucky.h86007665.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) ![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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/45096ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.Hotel-Information) 10/10 Exceptional (11) "Great stay and very clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan L. CA $157 CA $316 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.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) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/e4bb3cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034704/d588f9c3.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-503-175LEXWalk-To-Rupp-Arena.h91034704.Hotel-Information) 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) M M. CA $144 CA $272 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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/92000000/91040000/91034800/91034708/e8cf9444.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) ![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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-507-175-LEXWalk-To-Rupp-Arena.h91034708.Hotel-Information) 9.6/10 Exceptional (33) "Location, location, location! Great views of Main Street from the bedrooms and living rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fisher S. CA $157 CA $316 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-507-175-LEXWalk-To-Rupp-Arena.h91034708.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/92000000/91020000/91010900/91010891/575d6907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91010900/91010891/1a27c097.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-604-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010891.Hotel-Information) 9.8/10 Exceptional (12) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian M. CA $163 CA $328 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Lexington-Hotels-604-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010891.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/a24383fe.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) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/ec1d548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-502-175-LEXWalk-To-Rupp-Arena.h91010326.Hotel-Information) 9.0/10 Wonderful (2) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen S. CA $135 CA $262 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-502-175-LEXWalk-To-Rupp-Arena.h91010326.Hotel-Information) ![Smart TV, offices](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034700/67d102bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034700/7510a654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034700/196d5cb1.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/92000000/91040000/91034700/91034700/e639a531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-505-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034700.Hotel-Information) 10/10 Exceptional (1) "I don't have a single complaint. I enjoyed my stay very much! It was exactly as advertised. If I find myself in Lexington again, I would love to stay here again. 10/10" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex A. CA $144 CA $272 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-505-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034700.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034698/99cd82ea.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/92000000/91040000/91034700/91034698/b4fb8747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-501-175-LEXWalk-To-Rupp-Arena.h91034698.Hotel-Information) 8.8/10 Excellent (11) "Convenient, clean, and easy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracey H. CA $144 CA $272 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-501-175-LEXWalk-To-Rupp-Arena.h91034698.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) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/98000000/97010000/97001000/97000993/1cec5556.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) ### Condo in Downtown Lexington [](https://www.expedia.ca/Lexington-Hotels-The-Gatsby-Getaway-Quiet-Condo-Hotel-On-Main-St-Walkable-Downtown-Lexington.h97000993.Hotel-Information) 9.8/10 Exceptional (16) "Great location. Easy check in process. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim Y. CA $135 CA $262 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lexington-Hotels-The-Gatsby-Getaway-Quiet-Condo-Hotel-On-Main-St-Walkable-Downtown-Lexington.h97000993.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=2026-01-11&endDate=2026-01-12®ionId=7876&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 ![Home2 Suites by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/58000000/57490000/57487400/57487334/f62e7bf5_y.jpg) ### Home2 Suites by Hilton Lexington Hamburg 10/10 Excellent "Friendly and helpful staff, great breakfast, excellent location - very close to I75 and a lot of dining options close by, rooms are spacious and clean. " [](https://expedia.ca/Panacea-Hotels-Home2-Suites-By-Hilton-Lexington-Hamburg.h57487334.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Check in staff were terrific, very helpful with local recommendations for walking park and dinner options. Great fitness center and quiet clean rooms. Highly recommend " [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Holiday Inn Express Lexington East - Winchester by IHG](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/a8fad05c_y.jpg) ### Holiday Inn Express Lexington East - Winchester by IHG 10/10 Excellent "Just stayed one night but it was a very clean hotel. Everything smelt good good, staff was very friendly, and breakfast wasnt bad at all for a hotel. Will stay there again next time in that area." [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Very clean room" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Origin Lexington a Wyndham Hotel](https://images.trvl-media.com/lodging/34000000/33800000/33790700/33790682/7bb47690_y.jpg) ### Origin Lexington a Wyndham Hotel 10/10 Excellent "Great staff and facility. " [](https://expedia.ca/Lexington-Hotels-Origin-Hotel-Lexington.h33790682.Hotel-Information) ![Candlewood Suites Lexington Medical District by IHG](https://images.trvl-media.com/lodging/69000000/68050000/68049000/68048979/9303a1c8_y.jpg) ### Candlewood Suites Lexington Medical District by IHG 10/10 Excellent "Great!" [](https://expedia.ca/Lexington-Hotels-Candlewood-Suites-Lexington-Medical-District.h68048979.Hotel-Information) ![Staybridge Suites Lexington S Medical Ctr Area by IHG](https://images.trvl-media.com/lodging/77000000/76790000/76787000/76786917/0099ee0d_y.jpg) ### Staybridge Suites Lexington S Medical Ctr Area by IHG 10/10 Excellent "Clean and quiet" [](https://expedia.ca/Lexington-Hotels-Staybridge-Suites-Lexington-S-Medical-Ctr-Area.h76786917.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Clean rooms" [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.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 10/10 Excellent "We were only there for 6 hours, but they upgraded our room to a suit.. it was clean and conveniently located to the highway and restaurants.. gas station also" [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 229 | | ----------------- | ---------------- | | Accommodation | 54 Condo Rentals | | Lowest Price | CA $193 | | Highest Price | CA $443 | ## Frequently asked questions ### Why book your condo in Winchester with Expedia? ### How can I find cheap condos in Winchester? ### What is there to do in Winchester near my condo? ## Explore a world of travel with Expedia - 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