Title: Windsor Vacation Home Rentals from CA $388: 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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2026-01-02&endDate=2026-01-04&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/540b4e15.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) "Perfect place to stay to visit my daughter who lives in East Madison. Quiet neighborhood. Easy access to Madison and airport. House was equipped with what we needed--my daughter and me. Beds were VERY comfortable. We will be returning in October for another visit. Owner as so prompt to address any needs we had. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice A. CA $211 CA $648 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/d1a066eb.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) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116610000/116600600/116600540/4c73ba82.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) "The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia M. [](https://www.expedia.ca/Madison-Hotels-Private-Pool-HOT-TUB-Sauna-Game-Room-Pets.h116600540.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/41b16ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/cc95340c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/16f3436f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/27d8ceb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub - King Suite - Game Room - Large Groups Sun Prairie 10/10 Exceptional (11) "We had a great visit " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer D. [](https://www.expedia.ca/Sun-Prairie-Hotels-AMazing-Place-Summary.h111233952.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) ![Dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/10858971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/66c9c7eb.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) ### Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown! Monona 9.8/10 Exceptional (46) "We absolutely loved this place! Perfect spot with a pier on the water. My kids were catching fish within minutes. The house was perfect and Jake couldn’t have been easier to work with. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark G. CA $335 CA $708 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103060000/103055100/103055012/37e1c960.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) ### Madison Home | Near Quarry Ridge Trails Fitchburg 10/10 Exceptional (16) "Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie S. CA $454 CA $1,105 total includes taxes & fees Nov 9 - Nov 10 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/b9d1751e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84050000/84049300/84049281/82e34e45.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) "Great property, great location… with awesome dining and shopping options - a short drive to Madison without the congestion of being in Madison downtown. Tami was very helpful. Would definitely come back! Thanks Tami for a wonderful stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Smitha S. CA $492 CA $849 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Madison-Hotels-Entire-3-Bedroom-With-Fireplace-Sleeps-12.h84049281.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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141625/66efad89.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) ![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) "Our stay at The Saddlery was great. The check in process was easy and the communication was amazing. I had missed adding parking to our reservation and I was notified to confirm if parking was needed or not. The building and room was clean and up to date. The room was also nice and quiet for a great nights rest. Highly recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NICOLE R. CA $350 CA $456 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Madison-Hotels-One-Bedroom-King-With-Office-With-Views-Of-Lake-Monona-In-The-Heart-Of-Downtown.h109141625.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/5f34bdb6.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) ![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/64676f39.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 (10) "Check-In was easy. The house was very clean and organized. Plenty of room for all our guests. Would definitely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle L. CA $464 CA $803 total includes taxes & fees Nov 6 - Nov 7 [](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/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) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/f8090f44.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) ### Doty ★ Walk to Everything -Hotel Quality- Downtown Downtown Madison 9.8/10 Exceptional (35) "Great location, family friendly. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah S. CA $301 CA $490 total includes taxes & fees Nov 20 - Nov 21 [](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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/1b348406.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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141636/1c6d7a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Queen in the heart of downtown. Downtown Madison CA $294 CA $388 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Madison-Hotels-Studio-Queen-In-The-Heart-Of-Downtown.h109141636.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) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109150000/109141700/109141632/5766f31f.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 $294 CA $388 total includes taxes & fees Nov 30 - Dec 1 [](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=2025-11-19&endDate=2025-11-20®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 ![Days Inn by Wyndham Madison NE/Windsor](//images.trvl-media.com/lodging/1000000/80000/79700/79658/159b50d0_y.jpg) ### Days Inn by Wyndham Madison NE/Windsor 10/10 Excellent "Easy parking and easy to check in" [](https://expedia.ca/Madison-Hotels-Days-Inn-By-Wyndham-Madison-NEWindsor.h79658.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 "Check in was easy, the room was super clean and cute, great amenities, close to the Sylvee and other bars/restaurants and the lake. Would stay again!! " [](https://expedia.ca/Madison-Hotels-The-Dylin-By-Locale.h110849795.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 "Clean spacious and convenient location" [](https://expedia.ca/Madison-Hotels-Best-Western-East-Towne-Suites.h9095.Hotel-Information) ![The Madison Concourse Hotel and Governor's Club](//images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg) ### The Madison Concourse Hotel and Governor's Club 10/10 Excellent "Room was clean, check in and out was simple" [](https://expedia.ca/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information) ![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 "The room was great — bed was very comfortable. I enjoyed having a nice front lounge area with couches so that I could take a break from the room. Love the remodel!" [](https://expedia.ca/Madison-Hotels-Country-Inn-Suites-By-Radisson.h1105512.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 "The hotel was very clean and cute! Breakfast was also good, it would be nice to get more towels but I did read the mirror sign. Also our full body mirror was missing but overall great stay! For the first time it was a good hotel I will be staying again soon! And close to restaurants and felt safe ! Nice staff too! " [](https://expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-South.h59957100.Hotel-Information) ![DoubleTree by Hilton Madison East](//images.trvl-media.com/lodging/1000000/10000/3200/3157/a90c37bb_y.jpg) ### DoubleTree by Hilton Madison East 10/10 Excellent "The staff were super friendly. There’s lots of restaurants and a mall within walking distance. Not far from the airport. " [](https://expedia.ca/Madison-Hotels-DoubleTree-By-Hilton-Madison-East.h3157.Hotel-Information) ![Baymont by Wyndham Madison West/Middleton WI West](//images.trvl-media.com/lodging/1000000/50000/40100/40004/75db6fc0_y.jpg) ### Baymont by Wyndham Madison West/Middleton WI West 10/10 Excellent "Nice place. " [](https://expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-WestMiddleton-WI-West.h40004.Hotel-Information) ![Best Western Plus InnTowner Madison](//images.trvl-media.com/lodging/1000000/10000/2000/1919/37b6debe_y.jpg) ### Best Western Plus InnTowner Madison 10/10 Excellent "Every was very nice" [](https://expedia.ca/Madison-Hotels-Best-Western-Plus-InnTowner-Madison.h1919.Hotel-Information) ## Find out more about Windsor ## Windsor Vacation Homes information | Number of reviews | 143 | | --- | --- | | Accommodation | 98 Vacation Homes | | Lowest Price | CA $388 | | Highest Price | CA $1,105 | ## 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) - 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