Windsor Vacations from $505
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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.
Valued Stay Aloha
Carpenter Ridgeway
Price was $603, price is now $505 per person
$505
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
7.6/10 Good! (282 reviews)
Great staff, cute little place. Definitely not the Ritz but the price point can't be argued. You can tell they are trying - it was clean, safe and quiet.
Reviewed on Jan 14, 2026
Hilton Madison Monona Terrace
Downtown Madison
Price was $1,053, price is now $782 per person
$782
per person
Mar 14 - Mar 21
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
8.6/10 Excellent! (1,004 reviews)
Courteous staff, very clean. Comfortable bed. Super convenient to get to Menona Terrace. The only drawback at all was the furnace in room 421 was too noisy.
Reviewed on Jan 20, 2026
Embassy Suites By Hilton Madison Downtown
Downtown Madison
Price was $1,158, price is now $925 per person
$925
per person
Mar 14 - Mar 21
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
9.8/10 Exceptional! (430 reviews)
The place was super nice! Very clean and well staffed with very friendly helpful people. Loved our stay
Reviewed on Feb 6, 2026
Comfort Inn & Suites Madison East Interstate I-90
Price was $729, price is now $596 per person
$596
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
8.8/10 Excellent! (580 reviews)
Clean room staff was great. Shower made a lot of noise. My grandson would not even use it.
Reviewed on Feb 1, 2026
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.
Camp Randall Stadium
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.
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.
What to do in Windsor
Murmurs of Mourning & Murder: Madison Ghost Tour
$32
per adult
Windsor Hotel Deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $65 total per night from Feb 10 to Feb 11
$65 total
Feb 10 - Feb 11
Total with taxes and fees
7/10 Good! (1,002 reviews)
Place was clean, staff were polite.
Reviewed on Feb 3, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $161 total per night from Feb 8 to Feb 9
$161 total
Feb 8 - Feb 9
Total with taxes and fees
9.4/10 Exceptional! (3,477 reviews)
Great as always
Reviewed on Feb 3, 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $65 total per night from Feb 9 to Feb 10
$65 total
Feb 9 - Feb 10
Total with taxes and fees
8/10 Very Good! (1,157 reviews)
It was great!
Reviewed on Feb 2, 2026
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, Overture Center for the Arts and Orpheum Theater |
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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.
