Title: Book the Best Hotels with POOL in Windsor in 2026 | 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) ![Right off the highway, Mousehouse is a must visit for a quirky and fun stop that rewards visitors with delicious cheese and local brews. ](https://images.trvl-media.com/place/180667/68427fa4-e863-4d45-b589-b87b79708a6d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Joel Holland ![](https://images.trvl-media.com/place/180667/68427fa4-e863-4d45-b589-b87b79708a6d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 availability on Windsor Hotels with a Pool Tonight [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2026-01-19&endDate=2026-01-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2026-01-20&endDate=2026-01-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=180667&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/839b5a09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/3be88b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/159b50d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/411092d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Madison NE/Windsor [](https://www.expedia.ca/Madison-Hotels-Days-Inn-By-Wyndham-Madison-NEWindsor.h79658.Hotel-Information) Windsor 7.2/10 Good (1,002 reviews) "Friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kateri CA $86 CA $91 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Madison-Hotels-Days-Inn-By-Wyndham-Madison-NEWindsor.h79658.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/28000000/27710000/27705600/27705527/25d87fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27710000/27705600/27705527/426ef3c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/28000000/27710000/27705600/27705527/6558cdf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/28000000/27710000/27705600/27705527/6290d323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Oregon - Madison [](https://www.expedia.ca/Oregon-Hotels-Sleep-Inn-Suites-Oregon-Madison.h27705527.Hotel-Information) Oregon 9.4/10 Exceptional (364 reviews) "Love this hotel, they have the best front desk staff. Friendly, helpful and aways glad to see you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DENISE CA $105 CA $119 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Oregon-Hotels-Sleep-Inn-Suites-Oregon-Madison.h27705527.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/62500/62456/45d40477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/62500/62456/e2f21e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62500/62456/fc1c8a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/62500/62456/f20c3ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Madison, WI [](https://www.expedia.ca/Madison-Hotels-Country-Inn-Suites-By-Radisson.h62456.Hotel-Information) Monona 8.6/10 Excellent (1,000 reviews) "Great place clean friendly great food" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kris CA $106 CA $121 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Madison-Hotels-Country-Inn-Suites-By-Radisson.h62456.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/4d329710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/c9dcd645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/ec63abd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/w3836h2556x2y2-00aa8c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Madison-West [](https://www.expedia.ca/Madison-Hotels-Hampton-Inn-Suites-Madison-West.h2134982.Hotel-Information) Madison 9.0/10 Wonderful (1,008 reviews) "Room was spotless and staff was very friendly/helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary CA $102 CA $117 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Madison-Hotels-Hampton-Inn-Suites-Madison-West.h2134982.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/68bdf7e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/3e13d2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/4adfcbcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/8204d66c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Madison West/Middleton WI West [](https://www.expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-WestMiddleton-WI-West.h40004.Hotel-Information) Junction Ridge 8.0/10 Very good (1,140 reviews) "Nice place and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $85 CA $98 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-WestMiddleton-WI-West.h40004.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/e8164f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/62122329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/d7e153c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/0f75cbcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Madison American Center [](https://www.expedia.ca/Madison-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Madison-American-Center.h66424.Hotel-Information) Madison 8.2/10 Very good (1,406 reviews) "friendly staff good breakfast decent price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy CA $105 CA $122 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Madison-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Madison-American-Center.h66424.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/550000/548500/548482/fb36887f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/1000000/550000/548500/548482/75e21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/550000/548500/548482/4fb72be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/550000/548500/548482/a0df56d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Hotel & Suites Madison West - Middleton by IHG [](https://www.expedia.ca/Madison-Hotels-Holiday-Inn-Hotel-Suites-Madison-West.h548482.Hotel-Information) Junction Ridge 8.6/10 Excellent (467 reviews) "everything was perfect for our gathering and yes breakfast was fabulous" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $110 CA $127 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Madison-Hotels-Holiday-Inn-Hotel-Suites-Madison-West.h548482.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/52000000/51480000/51477800/51477790/16d8953e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51480000/51477800/51477790/9c3e1c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/52000000/51480000/51477800/51477790/62f152cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/52000000/51480000/51477800/51477790/869e0db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Madison West - Middleton by IHG [](https://www.expedia.ca/Madison-Hotels-Holiday-Inn-Express-And-Suites-Madison-West-Middleton.h51477790.Hotel-Information) Middleton 9.6/10 Exceptional (643 reviews) "The room, pool area and free breakfast are always excellent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $106 CA $120 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Madison-Hotels-Holiday-Inn-Express-And-Suites-Madison-West-Middleton.h51477790.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/70000000/69570000/69566700/69566609/fda3f586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/70000000/69570000/69566700/69566609/c78fbfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69570000/69566700/69566609/763cb164.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/70000000/69570000/69566700/69566609/793d196f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Madison West/Middleton [](https://www.expedia.ca/Madison-Hotels-TownePlace-Suites-By-Marriott-Madison-WestMiddleton.h69566609.Hotel-Information) Middleton 9.4/10 Exceptional (147 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $134 CA $152 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Madison-Hotels-TownePlace-Suites-By-Marriott-Madison-WestMiddleton.h69566609.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/55000000/54850000/54842100/54842068/b51a943d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/55000000/54850000/54842100/54842068/083c56f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/55000000/54850000/54842100/54842068/995106de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/55000000/54850000/54842100/54842068/8a63e034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Stoughton [](https://www.expedia.ca/Madison-Hotels-Tru-By-Hilton-Stoughton.h54842068.Hotel-Information) Stoughton 9.0/10 Wonderful (445 reviews) "Great place to stay, really enjoyed it " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) stanley james CA $100 CA $114 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Madison-Hotels-Tru-By-Hilton-Stoughton.h54842068.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=2026-02-02&endDate=2026-02-03®ionId=180667&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hotel Reviews ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg) ### The Madison Concourse Hotel and Governor's Club 10/10 Excellent "Convenient location and clean hotel " [](https://expedia.ca/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information) ![DoubleTree by Hilton Madison East](https://images.trvl-media.com/lodging/1000000/10000/3200/3157/a90c37bb_y.jpg) ### DoubleTree by Hilton Madison East 10/10 Excellent "Clean and courteous staff." [](https://expedia.ca/Madison-Hotels-DoubleTree-By-Hilton-Madison-East.h3157.Hotel-Information) ![DoubleTree by Hilton Madison Downtown](https://images.trvl-media.com/lodging/1000000/20000/12000/11944/7654de65_y.jpg) ### DoubleTree by Hilton Madison Downtown 10/10 Excellent "Staff was wonderful, room exceeded expectations" [](https://expedia.ca/Madison-Hotels-DoubleTree-By-Hilton-Madison-Downtown.h11944.Hotel-Information) ![Hampton Inn & Suites Madison / Downtown](https://images.trvl-media.com/lodging/7000000/6850000/6842700/6842611/13390bcb_y.jpg) ### Hampton Inn & Suites Madison / Downtown 10/10 Excellent "It was easy to get anywhere downtown. When I needed safety pins, the front desk people got me some " [](https://expedia.ca/Madison-Hotels-Hampton-Inn-Suites-Madison-Downtown.h6842611.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Madison American Center](https://images.trvl-media.com/lodging/1000000/70000/66500/66424/d7e153c1_y.jpg) ### La Quinta Inn & Suites by Wyndham Madison American Center 10/10 Excellent "Friendly staff Very clean" [](https://expedia.ca/Madison-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Madison-American-Center.h66424.Hotel-Information) ![The Edgewater](https://images.trvl-media.com/lodging/1000000/20000/14900/14843/927bfdc3_y.jpg) ### The Edgewater 10/10 Excellent "Room spotless, super hi quality interior and bedding. Room location was 1/8 a mile from front desk with multiple elevators. Third party booking always gets treated badly is my experience. " [](https://expedia.ca/Madison-Hotels-The-Edgewater.h14843.Hotel-Information) ![Hyatt Place Madison Downtown](https://images.trvl-media.com/lodging/4000000/3350000/3348100/3348068/w3840h2557x0y3-cfd232da_y.jpg) ### Hyatt Place Madison Downtown 10/10 Excellent "Staff was amazing, breakfast had good options and was kept fresh. " [](https://expedia.ca/Madison-Hotels-Hyatt-Place-Madison-Downtown.h3348068.Hotel-Information) ![Hilton Madison Monona Terrace](https://images.trvl-media.com/lodging/1000000/580000/575600/575515/c7c31566_y.jpg) ### Hilton Madison Monona Terrace 10/10 Excellent "Excellent staff, excellent location, and exceptional food/bar on site. " [](https://expedia.ca/Madison-Hotels-Hilton-Madison-Monona-Terrace.h575515.Hotel-Information) ![Baymont by Wyndham Madison West/Middleton WI West](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/75db6fc0_y.jpg) ### Baymont by Wyndham Madison West/Middleton WI West 10/10 Excellent "Room.was spotless, " [](https://expedia.ca/Madison-Hotels-Baymont-By-Wyndham-Madison-WestMiddleton-WI-West.h40004.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Windsor? ### What is there to see and do in Windsor? ### When is the best time to book a hotel with a pool in Windsor? ## 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) - [Cheap Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Cheap-Hotels.0-0-d6338039-tCheapHotels.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Burke ](https://www.expedia.ca/Burke-Madison-Hotels-Boutique-Hotel.0-n6340773-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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