Title: Windsor Vacation Packages 2026 from $665 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx180667)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d180667.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d180667.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d180667.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d180667.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations from $665 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Pink-Elephant-De-Forest.d553248621532659085.Vacation-Attraction), [Sun Prairie Golf Course](https://www.expedia.com/Sun-Prairie-Golf-Course-Sun-Prairie.d553248621561164834.Vacation-Attraction) and [Token Creek Park](https://www.expedia.com/Token-Creek-Park-Madison.d553248621554184985.Vacation-Attraction). Browse Expedia's extensive range of travel options and book your dream vacation to Windsor today. ## The Latest Windsor vacation packages Price found within the past 48 hours. Click for updated prices. ![The Edgewater](https://images.trvl-media.com/lodging/1000000/20000/14900/14843/96fe33c7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Edgewater Downtown Madison $665 per person May 22 - May 24 found 1 day ago Roundtrip flight included New York (NYC) to Madison (MSN) 9.2/10 Wonderful! (1,000 reviews) Amazing view of the lake with great room service. The staff is very friendly and helpful. Loved staying here. Reviewed on Mar 21, 2026 ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/5fd64d1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Madison Concourse Hotel and Governor's Club Downtown Madison $834 per person Jun 12 - Jun 16 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Madison (MSN) 9.4/10 Exceptional! (3,548 reviews) Very helpful front desk staff. We drove down. No airport shuttle was needed. Reviewed on Mar 24, 2026 ![Graduate by Hilton Madison](https://images.trvl-media.com/lodging/1000000/20000/14400/14397/1f9877bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton Madison Downtown Madison $1,051 per person Jun 2 - Jun 5 found 1 day ago Roundtrip flight included Atlanta (ATL) to Madison (MSN) 9/10 Wonderful! (1,000 reviews) Staff is exceptional. Super helpful and accommodating. Great location. Very happy with my stay. Reviewed on Mar 14, 2026 ![The Saddlery Madison Downtown](https://images.trvl-media.com/lodging/97000000/96210000/96202100/96202081/f5565d76_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Saddlery Madison Downtown Downtown Madison $794 per person May 22 - May 24 found 1 day ago Roundtrip flight included New York (NYC) to Madison (MSN) 9.2/10 Wonderful! (81 reviews) Clean and nice property Reviewed on Mar 21, 2026 ![Hotel Ruby Marie](https://images.trvl-media.com/lodging/1000000/800000/796500/796453/w1020h675x1y0-5cab3066_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Ruby Marie Downtown Madison $819 per person Jun 12 - Jun 16 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Madison (MSN) 9.4/10 Exceptional! (980 reviews) I left before the breakfast was served at 8:00\. It would be nice if they started serving breakfast earlier. Reviewed on Mar 14, 2026 Don't see what you're looking for? See all available trips from Columbus to Windsor [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-24/2026-05-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Windsor Hotel Deals ![Days Inn by Wyndham Madison NE/Windsor](https://images.trvl-media.com/lodging/1000000/80000/79700/79658/839b5a09_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 $68 nightly $72 total Mar 29 - Mar 30 Total with taxes and fees 7.2/10 Good! (1,001 reviews) Whirlpool was murky Breakfast was very anemic Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=79658&PinnedHotelID=79658&HadPinnedHotel=true®ionId=180667) ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/5fd64d1f_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 $139 nightly $161 total Mar 29 - Mar 30 Total with taxes and fees 9.4/10 Exceptional! (3,590 reviews) Very helpful front desk staff. We drove down. No airport shuttle was needed. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=180667) ![Best Western Plus InnTowner Madison](https://images.trvl-media.com/lodging/1000000/10000/2000/1919/f47bad39_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus InnTowner Madison 2424 University Avenue Madison WI Fully refundableReserve now, pay when you stay $126 nightly $146 total Mar 29 - Mar 30 Total with taxes and fees 9.2/10 Wonderful! (1,003 reviews) Nice place, a little run down, full car parking spaces Reviewed on Mar 14, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=1919&PinnedHotelID=1919&HadPinnedHotel=true®ionId=180667) [See all 406 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F25%2F2026&endDate=3%2F26%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. ## Find the Best Windsor Vacation Packages ## Windsor Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Closest Airport | Dane County Regional Airport (MSN) | | Population | 3,600 | | Max Temp Winter | 25ºF | | Max Temp Summer | 75ºF | | Top Sights | [Henry Vilas Zoo](https://www.expedia.com/Henry-Vilas-Zoo-Madison.d6068337.Vacation-Attraction), [Overture Center for the Arts](https://www.expedia.com/Overture-Center-For-The-Arts-Downtown-Madison.d6068323.Vacation-Attraction) and [Orpheum Theater](https://www.expedia.com/Orpheum-Theater-Downtown-Madison.d6260969.Vacation-Attraction) | 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations 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