Title: Windsor Vacation Packages 2026 from $661 | 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 $661 ## 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. ![Valued Stay Aloha](https://images.trvl-media.com/lodging/91000000/90980000/90970700/90970675/043ab3da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Valued Stay Aloha Carpenter Ridgeway $661 per person May 6 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Madison (MSN) 7.6/10 Good! (310 reviews) Great place to stay. Clean rooms! Nice staff. Reviewed on Mar 23, 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 Save 100% on your flight $2,035 per person May 6 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) 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 ![Hilton Garden Inn Madison West/Middleton](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101843/bcd06f44_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Madison West/Middleton Save 100% on your flight $1,318 per person May 6 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Madison (MSN) 9/10 Wonderful! (1,007 reviews) Comfortable bed and good in house amenities like a bar/restaurant and pool/hot tub. The family friendly nature is very much prioritized, with large families with multiple children taking over the common spaces like to pool and lounge area. The sofa mattress was stained with no option to move to a new room, we weren’t given enough bedding or towels for the number of guests, the pool towels were consistently out, the bathroom door in our room didn’t latch, a spring came off the sofa bed and the hallways smelled like weed. Underwhelming stay. Reviewed on Mar 22, 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 $994 per person Jun 6 - Jun 13 found 1 hour 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 ![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 Save 100% on your flight $1,865 per person May 6 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Madison (MSN) 8.6/10 Excellent! (1,003 reviews) Great location, clean hotel, just disappointed in the nightly parking fee Reviewed on Mar 24, 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/2026-04-25/2026-05-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Windsor ![Cool street art in Madison, Wisconsin](https://images.trvl-media.com/place/2424/f69833fb-8cae-4e95-9067-d9e88cfd3e67.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Wisconsin-Madison 4.5/5(895 reviews) Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.com/University-Of-Wisconsin-Madison-Campus-Area.d6068319.Vacation-Attraction) ![Historic Arched Entry to Camp Randall Stadium](https://images.trvl-media.com/place/6068321/9bfab1dd-b2f6-4e5a-b41c-fc5a5c133859.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Camp Randall Stadium 4.5/5(313 reviews) Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.com/Camp-Randall-Stadium-Madison.d6068321.Vacation-Attraction) ![This is great focal point for Madison!](https://images.trvl-media.com/place/2424/4c5d1f17-7c10-4510-80dc-89a2a8421a4f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wisconsin State Capitol 4.5/5(782 reviews) After visiting Wisconsin State Capitol, make a plan to see the other sights and activities in Madison. Discover the area's top-notch restaurants and its entertainment choices. [](https://expedia.com/Wisconsin-State-Capitol-Downtown-Madison.d6068325.Vacation-Attraction) ### What to do in Windsor ![Murmurs of Mourning & Murder: Madison Ghost Tour](https://mediaim.expedia.com/localexpert/46586124/2a33450c-333d-4173-a3af-46ad1464f49a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Murmurs of Mourning & Murder: Madison Ghost Tour $40 per adult [](https://expedia.com/things-to-do/murmurs-of-mourning-murder-madison-ghost-tour.a46586124.activity-details) ![Trolley Pub Public Tour](https://mediaim.expedia.com/localexpert/48956593/e77baf26-9704-49f2-9956-66027f0d5446.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Trolley Pub Public Tour $45 per adult [](https://expedia.com/things-to-do/trolley-pub-public-tour.a48956593.activity-details) [See all activities in Windsor](https://expedia.com/things-to-do/search?rid=180667) ## 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! (3,576 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 $117 nightly $135 total Mar 30 - Mar 31 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) everything was perfect. the restaurant within the hotel had great quality. the room was clean. the staff were great. i was impressed that they had free laundry machine and dryer for guests to use. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%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%2F26%2F2026&endDate=3%2F27%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) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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 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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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