Title: Windsor Condo Rentals from CA $177 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d6005427.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Windsor from CA $177 - ![](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 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor condo rentals ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) Williamstown 8.8/10 Excellent (2,204 reviews) "I great place to stay!!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Maricel CA $145 CA $177 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/cdf98da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/7ca2d407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/0b131f87_edited_aacc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/bf324bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) Hancock 9.0/10 Wonderful (2 reviews) "very nice and roomy! really enjoyed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shack M. CA $191 CA $418 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/3e2af0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/c1de7213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/45a94106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/87c90776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) Hancock 7.2/10 Good (11 reviews) "Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PK N. CA $191 CA $471 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h804x0y7-b7678d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE - 1BR Country Condo @ Jiminy Peak [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) Hancock 10/10 Exceptional (14 reviews) "lovely place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy P. CA $224 CA $543 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.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=2026-01-25&endDate=2026-01-26®ionId=6005427&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%2FWindsor-Condos.d6005427-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Condos.d6005427-aaCondos.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Perfectly Clean. Great Service. Beautiful Place!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "Really nice place staff " [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Extraordinary" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very good " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Very clean, modern hotel. Would definitely stay here again. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Absolutely fabulous!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Delicious sundae! Cozy fire!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ## Find out more about Windsor ## Windsor Condo Rentals information | Number of reviews | 2,228 | | ----------------- | ---------------- | | Accommodation | 45 Condo Rentals | | Lowest Price | CA $177 | | Highest Price | CA $543 | ## Frequently asked questions ### Why book your condo in Windsor with Expedia? ### How can I find cheap condos in Windsor? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Vacation Rental - More ways to book - [Beach Hotel Hotels in Adams ](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adams ](https://www.expedia.ca/Adams-Hotels-Cheap-Hotels.0-0-d6005393-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Adams ](https://www.expedia.ca/Adams-Hotels-Historic-Hotel.0-0-d6005393-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Adams ](https://www.expedia.ca/Adams-Hotels-Mountain-Hotels.0-0-d6005393-tMountainHotels.Travel-Guide-Filter-Hotels) - 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