Title: Windsor Vacation Home Rentals from CA $385: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d180667.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d180667.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d180667.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d180667.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d180667.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c709fbe10e401697c692bae65fdcfcc1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Joel Holland # Windsor Vacation Rentals ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windsor Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/b85875a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/94b7dd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/668ab00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/f90b098b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Duplex unit with WiFi in Cottage Grove Village of Cottage Grove 10/10 Exceptional (7) "Very nice duplex with everything you could need. Super quiet neighborhood. Would stay here again if in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt W. CA $210 CA $649 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141639/920cbe1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141639/3bdedced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141639/cfde82bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141639/9d7ad0a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### One Bedroom Queen in the heart of downtown. Downtown Madison 10/10 Exceptional (2) "We really enjoyed our stay and the close location to the capital. Great modern style and very functional " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandrines H. CA $292 CA $385 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Madison-Hotels-One-Bedroom-Queen-In-The-Heart-Of-Downtown.h109141639.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/c87bc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/3722bd3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/0743063b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/10858971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown! Monona 9.8/10 Exceptional (43) "Such a nice house! Great location and excellent amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carson M. CA $334 CA $701 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/5d9b88e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/f7b9beb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/468eeeb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/d1a066eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Pool - HOT TUB - Sauna - Game Room - Pets Sun Prairie 10/10 Exceptional (5) CA $565 CA $1,439 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Madison-Hotels-Private-Pool-HOT-TUB-Sauna-Game-Room-Pets.h116600540.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/8a317c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/5d22d043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/64676f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/c87e9887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown Sun Prairie 10/10 Exceptional (9) "The house was very clean and comfortable. We had a great experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelsie J. CA $462 CA $804 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Madison-Hotels-Citys-EDGE-Of-Madison-6-Miles-To-Downtown.h112243000.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/32f78388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/7edec21a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, printers](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/34a2e906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/2d3f3f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR/3BA Home | Dual Living Spaces Fitchburg 10/10 Exceptional (15) "Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim & Jeff T. CA $404 CA $1,048 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Madison-Hotels-3-BR-Executive-Home-Near-Madison-W-Nature-Trails-Madisons-Best-Nearby.h103055012.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/w506h683x259y0-0748895f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/f4c4e83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/b9d1751e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/w903h683x61y0-c813b14c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom with Fireplace - sleeps 12 Sun Prairie 9.8/10 Exceptional (15) "Plenty of blankets pillows bed were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly P. CA $490 CA $845 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Madison-Hotels-Entire-3-Bedroom-With-Fireplace-Sleeps-12.h84049281.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/6135cef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/199c30da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/e901e932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/517f1048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Doty ★ Walk to Everything -Hotel Quality- Downtown Downtown Madison 9.8/10 Exceptional (34) "Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mindi Z. CA $524 CA $784 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Madison-Hotels-Doty-Walk-To-Everything-Hotel-Quality-Downtown.h74124541.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/09863c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/13ba8e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/1b348406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/506de11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Queen in the heart of downtown. Downtown Madison CA $292 CA $386 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Madison-Hotels-Studio-Queen-In-The-Heart-Of-Downtown.h109141636.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141625/6f96a9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141625/034306ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141625/42beaa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141625/c86cc704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### One Bedroom King with Office with views of Lake Monona in the heart of downtown. Downtown Madison 10/10 Exceptional (2) "The place is beautiful and perfectly appointed with necessary equipment. Gorgeous view! Easy and convenient parking and check in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maggie C. CA $348 CA $457 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Madison-Hotels-One-Bedroom-King-With-Office-With-Views-Of-Lake-Monona-In-The-Heart-Of-Downtown.h109141625.Hotel-Information) ![1 bedroom](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141632/ba7312c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141632/c6da4919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141632/b0894410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141632/fafda11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### One Bedroom King with views of Lake Monona in the heart of downtown. Downtown Madison CA $306 CA $402 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Madison-Hotels-One-Bedroom-King-With-Views-Of-Lake-Monona-In-The-Heart-Of-Downtown.h109141632.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=2025-11-07&endDate=2025-11-08®ionId=180667&adults=2&lodging=VACATION_HOME&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%2FWindsor-Private-Vacation-Homes.d180667-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Private-Vacation-Homes.d180667-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Country Inn & Suites by Radisson, Madison West, WI](//images.trvl-media.com/lodging/2000000/1110000/1105600/1105512/ab6d47c8_y.jpg) ### Country Inn & Suites by Radisson, Madison West, WI 10/10 Excellent "Breakfast potatoes were terrible Who has potatoes with rosemary for breakfast disgusting no those are not breakfast potatoes however everything else was very nice." [](https://expedia.ca/Madison-Hotels-Country-Inn-Suites-By-Radisson.h1105512.Hotel-Information) ![The Dylin by Mint House](//images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/888b2e39_y.jpg) ### The Dylin by Mint House 10/10 Excellent "Free parking right along the street, very easy to get in and out of the building. Great location (<10 mins walk from the capital). Apartment was very clean and tidy, also provided bathroom toiletries. Would stay again!" [](https://expedia.ca/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Madison American Center](//images.trvl-media.com/lodging/1000000/70000/66500/66424/d7e153c1_y.jpg) ### La Quinta Inn & Suites by Wyndham Madison American Center 10/10 Excellent "Well maintained hotel and very clean. Staff were very friendly." [](https://expedia.ca/Madison-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Madison-American-Center.h66424.Hotel-Information) ![Best Western East Towne Suites](//images.trvl-media.com/lodging/1000000/10000/9100/9095/d6e92708_y.jpg) ### Best Western East Towne Suites 10/10 Excellent "Enjoyed the ease of access to and from the hotel. The staff was very friendly and professional." [](https://expedia.ca/Madison-Hotels-Best-Western-East-Towne-Suites.h9095.Hotel-Information) ![Best Western Premier Park Hotel](//images.trvl-media.com/lodging/8000000/7050000/7043100/7043069/4f17c333_y.jpg) ### Best Western Premier Park Hotel 10/10 Excellent "Perfect location" [](https://expedia.ca/Madison-Hotels-Best-Western-Premier-Park-Hotel.h7043069.Hotel-Information) ![Best Western West Towne Suites](//images.trvl-media.com/lodging/1000000/30000/25600/25566/5ae91cd1_y.jpg) ### Best Western West Towne Suites 10/10 Excellent "Awesome" [](https://expedia.ca/Madison-Hotels-Best-Western-West-Towne-Suites.h25566.Hotel-Information) ![Quality Inn & Suites Lodi I-90](//images.trvl-media.com/lodging/2000000/1010000/1000700/1000697/b8e3941b_y.jpg) ### Quality Inn & Suites Lodi I-90 10/10 Excellent "I was very please with my entire stay. Going a few miles outside of Madison WI was worth it. I had a great stay and the saved money." [](https://expedia.ca/Lodi-Hotels-Quality-Inn-Suites.h1000697.Hotel-Information) ![Baymont Inn & Suites by Wyndham Madison](//images.trvl-media.com/lodging/60000000/59960000/59957100/59957100/08c3cafb_y.jpg) ### Baymont Inn & Suites by Wyndham Madison 10/10 Excellent "It’s was very good " [](https://expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-South.h59957100.Hotel-Information) ![Motel 6 Madison, WI - East](//images.trvl-media.com/lodging/1000000/10000/1800/1719/b06e2cee_y.jpg) ### Motel 6 Madison, WI - East 10/10 Excellent "A regular visitor of this location. It’s convenient for my job." [](https://expedia.ca/Madison-Hotels-Motel-6-Madison.h1719.Hotel-Information) ## Find out more about Windsor ## Windsor Vacation Homes information | Number of reviews | 129 | | --- | --- | | Accommodation | 98 Vacation Homes | | Lowest Price | CA $385 | | Highest Price | CA $1,439 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Hotels near American Center](https://www.expedia.ca/American-Center-Hotels.0-l6161969-0.Travel-Guide-Filter-Hotels) - [B&B in Arlington](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d6338039-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Arlington](https://www.expedia.ca/Arlington-Guest-Houses.d6338039-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in Arlington](https://www.expedia.ca/Arlington-Motels.d6338039-aaMotels.Travel-Guide-Accommodation) - [Resorts in Arlington](https://www.expedia.ca/Arlington-Resort-Hotels.d6338039-aaResortHotels.Travel-Guide-Accommodation) - [B&B in Dane](https://www.expedia.ca/Dane-Bed-And-Breakfast.d3000461600-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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