Title: Windsor Vacation Packages & Trips 2026 from CA $422 | 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) ![](https://images.trvl-media.com/place/180667/68427fa4-e863-4d45-b589-b87b79708a6d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Joel Holland - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Windsor Vacation Lock in a Windsor vacation package and prepare to experience the highlights of this city. Think about staying in the neighborhood of Marquette, which is good for cycling, culture and fishing. You'll want to go sightseeing during your trip to Windsor. Find time for top attractions such as [Pink Elephant](https://www.expedia.ca/Pink-Elephant-De-Forest.d553248621532659085.Vacation-Attraction), [Sun Prairie Golf Course](https://www.expedia.ca/Sun-Prairie-Golf-Course-Sun-Prairie.d553248621561164834.Vacation-Attraction) and [Token Creek Park](https://www.expedia.ca/Token-Creek-Park-Madison.d553248621554184985.Vacation-Attraction). Browse Expedia's extensive range of travel options and book your dream vacation to Windsor today. ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Motel 6 Janesville, WI](https://images.trvl-media.com/lodging/1000000/1000000/996300/996269/40aef5f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 Janesville, WI CA $422 per person Apr 1 - Apr 3 found 11 hours ago Roundtrip flight included Toronto (YTO) to Madison (MSN) 7/10 Good! (827 reviews) I had to try three rooms before I got a good one first one had not even been cleaned second one the heater didn't work the third times a charm. It was average pretty cheap hotel the concierge was very helpful and apologetic Reviewed on Dec 16, 2025 ![Hilton Madison Monona Terrace](https://images.trvl-media.com/lodging/1000000/580000/575600/575515/c7c31566_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Madison Monona Terrace Downtown Madison CA $668 per person Feb 24 - Feb 26 found 2 hours ago Roundtrip non-stop flight included Buffalo (BUF) to Madison (MSN) 8.6/10 Excellent! (1,004 reviews) Man at the front desk was very helpful and friendly. Clean room in a great location. Bar was open late. Parking in the Wilson St Garage was easier and cheaper than on site parking. Overall, a great stay and we'll be back Reviewed on Dec 29, 2025 ![The Edgewater](https://images.trvl-media.com/lodging/1000000/20000/14900/14843/927bfdc3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Edgewater Downtown Madison CA $762 per person Feb 24 - Feb 26 found 2 hours ago Roundtrip non-stop flight included Buffalo (BUF) to Madison (MSN) 9.2/10 Wonderful! (1,003 reviews) Great customer service! Very luxurious stay! Reviewed on Jan 4, 2026 ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Madison Concourse Hotel and Governor's Club Downtown Madison CA $646 per person Feb 24 - Feb 26 found 2 hours ago Roundtrip non-stop flight included Buffalo (BUF) to Madison (MSN) 9.4/10 Exceptional! (3,305 reviews) Staff was amazing. It was very clean and had all the amenities that we needed. Reviewed on Jan 6, 2026 ![Valued Stay Aloha](https://images.trvl-media.com/lodging/91000000/90980000/90970700/90970675/c7c35d41_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Valued Stay Aloha Carpenter Ridgeway CA $526 per person Feb 24 - Feb 26 found 2 hours ago Roundtrip non-stop flight included Buffalo (BUF) to Madison (MSN) 7.6/10 Good! (282 reviews) Ignore the older reviews, this place has really turned around! The staff was nice and the room was clean. I plan on returning here next time my work sends me to Madison. Reviewed on Nov 14, 2025 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![Days Inn by Wyndham Madison NE/Windsor](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/159b50d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Madison NE/Windsor 6311 Rostad Dr Windsor WI Fully refundableReserve now, pay when you stay CA $86 CA $90 total Jan 11 - Jan 12 includes taxes & fees 7/10 Good! (1,008 reviews) Staff was rude Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=79658&PinnedHotelID=79658&HadPinnedHotel=true®ionId=180667) ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Madison Concourse Hotel and Governor's Club 1 W Dayton St Madison WI Fully refundableReserve now, pay when you stay CA $173 CA $200 total Jan 18 - Jan 19 includes taxes & fees 9.4/10 Exceptional! (3,418 reviews) We were not aware we had a free breakfast. We did have a brunch on Christmas morning that was good, waiters were very nice. This is the second survey you have sent me. I replied to the first with comments about the lack of housekeeping for the entire stay. Had we not contacted the front desk we would ... Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=180667) ![Hampton Inn & Suites Madison-West](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/w3835h2385x4y4-ff0bb2ca_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Madison-West 483 Commerce Dr Madison WI Fully refundableReserve now, pay when you stay CA $101 CA $116 total Jan 11 - Jan 12 includes taxes & fees 9/10 Wonderful! (1,011 reviews) The front dest staff were exceptional, always a smiling face and a welcoming greeting. The room was clean and comfortable. I am confused about the billing. I was charged, but also credited for more than the charge of the room. Reviewed on Jan 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=2134982&PinnedHotelID=2134982&HadPinnedHotel=true®ionId=180667) [See all 398 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F01%2F2026&endDate=10%2F01%2F2026®ionId=180667) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near American Center ](https://www.expedia.ca/American-Center-Hotels.0-l6161969-0.Travel-Guide-Filter-Hotels) - [Hotels near Dane County Regional ](https://www.expedia.ca/Dane-County-Regional-Airport-Hotels.0-aMSN-0.Travel-Guide-Filter-Hotels) - [Chalets in De Forest ](https://www.expedia.ca/De-Forest-Chalets.d180665-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in De Forest ](https://www.expedia.ca/De-Forest-Guest-Houses.d180665-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in De Forest ](https://www.expedia.ca/De-Forest-Hotels-Cheap-Hotels.0-0-d180665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in De Forest ](https://www.expedia.ca/De-Forest-Hotels-LGBT-Friendly-Hotel.0-0-d180665-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in De Forest ](https://www.expedia.ca/De-Forest-Hotels-Luxury-Hotel.0-0-d180665-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in De Forest ](https://www.expedia.ca/De-Forest-Hotels-Pet-Friendly-Hotel.0-0-d180665-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in De Forest ](https://www.expedia.ca/De-Forest-Hotels-Romantic-Hotel.0-0-d180665-tRomanticHotel.Travel-Guide-Filter-Hotels) - [De Forest Hotels ](https://www.expedia.ca/De-Forest-Hotels.d180665.Travel-Guide-Hotels) - [Motels in De Forest ](https://www.expedia.ca/De-Forest-Motels.d180665-aaMotels.Travel-Guide-Accommodation) - [Ski Hotels in Token Creek ](https://www.expedia.ca/Token-Creek-Madison-Hotels-Ski-Hotel.0-n6338152-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Token Creek Hotels ](https://www.expedia.ca/Token-Creek-Madison-Hotels.0-n6338152-0.Travel-Guide-Filter-Hotels) - [Flights from Dane County Regional ](https://www.expedia.ca/lp/airports/msn/flights-from-dane-county-regional-airport) - [Air Canada Halifax (YHZ) to Madison (MSN) flights ](https://www.expedia.ca/lp/flight-routes/air-canada-from-stanfield-intl-to-dane-county-regional/ac/yhz/msn) - [Flights from Bangor (BGR) to Madison (MSN) ](https://www.expedia.ca/lp/flights/bgr/msn/bangor-to-madison) - [Flights from Bellingham (BLI) to Madison (MSN) ](https://www.expedia.ca/lp/flights/bli/msn/bellingham-to-madison) - [Flights from Boston (BOS) to Madison (MSN) ](https://www.expedia.ca/lp/flights/bos/msn/boston-to-madison) - [Flights from Burlington (BTV) to Madison (MSN) ](https://www.expedia.ca/lp/flights/btv/msn/burlington-to-madison) - [Flights from Buffalo (BUF) to Madison (MSN) ](https://www.expedia.ca/lp/flights/buf/msn/buffalo-to-madison) - [Flights from Sault Ste. 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Olympus Water and Theme Park ](https://www.expedia.ca/Mt-Olympus-Water-And-Theme-Park-Wisconsin-Dells.d6094033.Vacation-Attraction) - [Noah's Ark Waterpark ](https://www.expedia.ca/Noahs-Ark-Waterpark-Wisconsin-Dells.d6094037.Vacation-Attraction) - [Olin Park ](https://www.expedia.ca/Olin-Park-Madison.d6292824.Vacation-Attraction) - [Paul Bunyan's Northwoods Lumberjack Show ](https://www.expedia.ca/Paul-Bunyans-Northwoods-Lumberjack-Show-Wisconsin-Dells.d6329236.Vacation-Attraction) - [Pirate's Cove Adventure Golf ](https://www.expedia.ca/Pirates-Cove-Adventure-Golf-Wisconsin-Dells.d6094039.Vacation-Attraction) - [South Madison Vacations ](https://www.expedia.ca/South-Madison.d6059908.Destination-Travel-Guides) - [Southern Wisconsin Vacations ](https://www.expedia.ca/Southern-Wisconsin.d553248635975749457.Destination-Travel-Guides) - [Timber Falls Adventure Park ](https://www.expedia.ca/Timber-Falls-Adventure-Park-Wisconsin-Dells.d6157680.Vacation-Attraction) - [Top Secret ](https://www.expedia.ca/Top-Secret-Wisconsin-Dells.d553248621558928139.Vacation-Attraction) - [Tower Hill State Park ](https://www.expedia.ca/Tower-Hill-State-Park-Spring-Green.d553248621561207065.Vacation-Attraction) - [Troll Beach ](https://www.expedia.ca/Troll-Beach-Stoughton.d553248621558012059.Vacation-Attraction) - [Verona Vacations ](https://www.expedia.ca/Verona.d178206.Destination-Travel-Guides) - [Wisconsin Dells Vacations ](https://www.expedia.ca/Wisconsin-Dells.d6059846.Destination-Travel-Guides) - [Wizard Quest ](https://www.expedia.ca/Wizard-Quest-Wisconsin-Dells.d6094051.Vacation-Attraction) - [Woodside Wisconsin Dells Center Dome ](https://www.expedia.ca/Woodside-Wisconsin-Dells-Center-Dome-Wisconsin-Dells.d553248627444927838.Vacation-Attraction) - [Rental cars Dane County Regional airport ](https://www.expedia.ca/Car-Rentals-In-Dane-County-Regional.d5133133.Car-Rental-Guide) \* Savings based on package bookings compared to the price of the same components booked separately. 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