Windsor Vacations from $433
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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, Sun Prairie Golf Course and Token Creek Park. 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.
Bluegreen Christmas Mountain Village, an Ascend Resort
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
8.2/10 Very Good! (116 reviews)
We had stayed in this property before, and again this trip did not disappoint!
Reviewed on Jul 22, 2025
DoubleTree by Hilton Madison East
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.4/10 Exceptional! (1,000 reviews)
Our only issue was that on our first day there was only 1 elevator working. The next day there were 2; however, there were also sooo many cheerleaders who came in for a camp. There were some long waits for the elevators.
Reviewed on Aug 5, 2025
Discover the most popular places to visit in Windsor
University of Wisconsin-Madison
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.
Capitol Square
You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.
Monona Terrace Community and Convention Center
Learn about the events happening at Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
What to do in Windsor
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
$26
per adult
Windsor Hotel Deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $72 total per night from Aug 10 to Aug 11
$72 total
Aug 10 - Aug 11
Total includes taxes and fees
7/10 Good! (925 reviews)
"It was a nice place to stay@"
Reviewed on Aug 4, 2025
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
$139 nightly
The price is $161 total per night from Aug 10 to Aug 11
$161 total
Aug 10 - Aug 11
Total includes taxes and fees
9.4/10 Exceptional! (2,950 reviews)
"Great location and excellent value. Having a restaurant and bar on site was a huge plus. Shuttle to the airport at 5 am was appreciated!"
Reviewed on Aug 5, 2025
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
$67 nightly
The price is $78 total per night from Sep 2 to Sep 3
$78 total
Sep 2 - Sep 3
Total includes taxes and fees
7.8/10 Good! (1,000 reviews)
"I can’t say enough great things about my stay at the Baymont Hotel West in Madison! From the moment I arrived, every staff member I encountered went above and beyond to make me feel welcome and taken care of. Their customer service is truly top-notch, friendly, professional, and always eager to help ..."
Reviewed on Aug 4, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.