Title: Winchester Condo Rentals from CA $218 | 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 $218 - ![](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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Browse Select Winchester Condo Rentals ![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) ![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) ![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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) M M. CA $153 CA $287 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lexington-Hotels-503-175LEXWalk-To-Rupp-Arena.h91034704.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105860200/105860169/543c328c.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) ### Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington Lexington CA $132 CA $394 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-Cozy-2-Bedroom-Condo-With-WiFi.h105860169.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/98000000/97010000/97001100/97001020/45096ab1.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 Downtown Lexington 10/10 Exceptional (11) "Delightful stay! Thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melinda S P. CA $175 CA $345 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.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) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/c68d03de.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) ![TV](https://images.trvl-media.com/lodging/97000000/96240000/96239500/96239461/80a86047.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 9.0/10 Wonderful (9) "The code to unlock the key was incorrect. We were stuck outside the rental for over 1 hour trying to connect with the owner and customer service. Was a frustrating and sloppy check in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriel P. CA $133 CA $240 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-This-Condominium-Is-A-1-Bedroom.h96239461.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/f7a1694e.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) ### 175 LEX - Stunning Downtown Views on Main Street! Downtown Lexington 9.8/10 Exceptional (42) "Very clean and convenient to Rupp arena " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy R. CA $161 CA $297 total includes taxes & fees Nov 30 - Dec 1 [](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) ![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) ![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) ### Graffiti Art Haus - Walk to Central Bank Arena Downtown Lexington 10/10 Exceptional (34) "Perfect place to stay for visiting downtown Lexington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. CA $110 CA $288 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lexington-Hotels-Cool-Condo-2-Blocks-To-Rupp-Distillery-District.h74114349.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) ![Interior](https://images.trvl-media.com/lodging/103000000/102070000/102065400/102065366/3c3441e9.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) ### Lex In The City - Downtown Condo Downtown Lexington 9.8/10 Exceptional (8) "The place was great. Good location downtown. The bed was one of the most comfortable I have had at a rental space. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David W. CA $161 CA $295 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-Lex-In-The-City-Downtown-Condo.h102065366.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) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/c163da2a.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) ![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) ### Quiet Downtown Lexington Bougie Apartment Downtown Lexington 9.6/10 Exceptional (4) "Everything was perfect. Would stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TRICIA H. CA $153 CA $285 total includes taxes & fees Nov 13 - Nov 14 [](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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102660000/102653100/102653067/1404c050.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) ![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102653100/102653067/654d8fcf.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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vince T. CA $153 CA $285 total includes taxes & fees Nov 13 - Nov 14 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99620000/99610100/99610080/51210968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College Georgetown 10/10 Exceptional (5) "Really appreciated the host touching base with us to be sure everything was going okay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy W. CA $224 CA $457 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-Man-OWar-Horse-Park-11-MinArk-30-MinWalk-Downtown.h99610080.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 9.2/10 Wonderful (12) "Everything was as described. Very spacious condo. Only reason I couldn't give it 5 stars is the air conditioner made a loud noise every 30 minutes or so which would wake us up." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob and Michelle G. CA $175 CA $349 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lexington-Hotels-504-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91010163.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) ![Interior](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/828de569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/87000000/86010000/86007700/86007665/304c8632.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) ### 1 Bedroom | Near the University of Kentucky. Lexington CA $160 CA $218 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Lexington-Hotels-1-Bedroom-Near-The-University-Of-Kentucky.h86007665.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/9dfcb411.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034703/6034810e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Walk to Rupp Arena Downtown Top Floor Downtown Lexington 9.8/10 Exceptional (20) "The place was nice, clean, in a great location walkable to anything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex B. CA $147 CA $279 total includes taxes & fees Nov 13 - Nov 14 [](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) ![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 (16) "The condo was perfect for our UK parents weekend stay! It was close to everything and the unit was clean and well stocked! Would recommend and will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary K. CA $167 CA $337 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lexington-Hotels-175-LEX-Spacious-Two-Bedroom-Near-Rupp-Arena.h96530516.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 (12) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian M. CA $175 CA $345 total includes taxes & fees Nov 13 - Nov 14 [](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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010400/91010326/cd788f05.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen S. CA $139 CA $268 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-502-175-LEXWalk-To-Rupp-Arena.h91010326.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) ![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) ![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 9.0/10 Wonderful (9) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $153 CA $285 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-501-175-LEXWalk-To-Rupp-Arena.h91034698.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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/cf46ae0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91034800/91034708/96732aab.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) ### 175 LEX - Spacious Two Bedroom Downtown Lexington Downtown Lexington 9.6/10 Exceptional (32) "We really liked this property. Good location and the apartment is very clean and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan R. CA $175 CA $345 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-507-175-LEXWalk-To-Rupp-Arena.h91034708.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034700/196d5cb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034700/0154d404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Walkable Downtown Lexington Condo Downtown Lexington 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 $161 CA $295 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-505-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034700.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034697/8d57ed3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034697/ac12c9b2.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/92000000/91040000/91034700/91034697/a0c2e338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91034700/91034697/ef9eef7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 175 LEX - Walkable Loft to Rupp Arena & Downtown! Downtown Lexington 9.4/10 Exceptional (15) "I was impressed by this home! Parking was easily accessible. The property was very clean and comfy. We were also in a prime location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $147 CA $279 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-603-175-LEX-Walk-To-Rupp-Arena-Dtown-High-Rise.h91034697.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=2025-11-26&endDate=2025-11-27®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 ![Hyatt Regency Lexington](//images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Clean. Nice and comfortable Rooms. Friendly staff." [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Hyatt Place Lexington](//images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "The room was very comfortable, sitting area was great, bed was very comfortable. " [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](//images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "The staff was very courteous " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![Tru by Hilton University Medical Center](//images.trvl-media.com/lodging/79000000/78010000/78004900/78004839/9823f52b_y.jpg) ### Tru by Hilton University Medical Center 10/10 Excellent "That was the fastest check in I’ve ever had. Thanks you. The staff was very nice and the room was very clean. The breakfast had good options." [](https://expedia.ca/Lexington-Hotels-Tru-By-Hilton-Lexington-University-Medical-Center.h78004839.Hotel-Information) ![Red Roof Inn Lexington South](//images.trvl-media.com/lodging/1000000/10000/5100/5077/a6cc1928_y.jpg) ### Red Roof Inn Lexington South 10/10 Excellent " Nice" [](https://expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-South.h5077.Hotel-Information) ![The Manchester ](//images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "Beautiful place on the inside. Staff was friendly. " [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/1000000/30000/27400/27364/25d8ec98_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Room was clean and staff friendly " [](https://expedia.ca/Lexington-Hotels-Comfort-Inn-Suites.h27364.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "The room was clean and comfortable. I enjoyed the warm breakfast!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.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 "Muy bueno " [](https://expedia.ca/Lexington-Hotels-GLo-Best-Western-Lexington.h123895.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 218 | | --- | --- | | Accommodation | 58 Condo Rentals | | Lowest Price | CA $218 | | Highest Price | CA $457 | ## Frequently asked questions ### Why book your condo in Winchester with Expedia? > Getting away shouldn't be difficult, so if you're on the lookout for condos at an affordable rate, Expedia has got your back. Keep costs down and select something small and affordable, or splurge on a luxury condo and spoil your favorite people. Our search filters make it a breeze to find a property in Winchester that matches your needs. ### How can I find cheap condos in Winchester? > A great way to score cheap condos in Winchester is with Expedia's useful filter tool. Narrow down your search results by budget, amenities and star rating to snag unbeatable prices in just a few clicks. ### What is there to do in Winchester near my condo? > Once you've settled into your hotel, venture out and discover the fantastic things Winchester has on offer. 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