Windsor Vacations from $247
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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.
Polynesian Hotel & Suites Wisconsin Dells/Lake Delton
Price was $326, price is now $247 per person
$247
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
5.8/10 (982 reviews)
Staff were curteous, room was fine. Bathroom was outdated and small. Pool facilities were closed but did get tickets to another indoor “waterpark” which was just a pool. Nonetheless the kids enjoyed it for a good price.
Reviewed on Nov 14, 2025
MainStay Suites Fitchburg - Madison
Price was $360, price is now $283 per person
$283
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
8.8/10 Excellent! (1,000 reviews)
The towels were dirty - 2 out of 3 of them had stains. The room smelled like smoke and air freshener. The coffee was not good. The shower screamed the whole time it was in use. Staff was great, though. Parking lot was not maneuverable several hours after winter storm.
Reviewed on Nov 30, 2025
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort
Price was $527, price is now $416 per person
$416
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
8.4/10 Very Good! (122 reviews)
How clean the room looks how nice the staff was
Reviewed on Dec 14, 2025
The Madison Concourse Hotel and Governor's Club
Downtown Madison
Price was $520, price is now $415 per person
$415
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9.4/10 Exceptional! (3,305 reviews)
They have one of the most comfortable beds and pillows I've ever felt. They are on my top 3 best sleeps.
Reviewed on Dec 21, 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
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 Dec 25 to Dec 26
$65 total
Dec 25 - Dec 26
Total with taxes and fees
7/10 Good! (1,000 reviews)
Very good staff, clean hotel and always something to do
Reviewed on Nov 27, 2025
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 Dec 28 to Dec 29
$161 total
Dec 28 - Dec 29
Total with taxes and fees
9.4/10 Exceptional! (3,381 reviews)
They have one of the most comfortable beds and pillows I've ever felt. They are on my top 3 best sleeps.
Reviewed on Dec 21, 2025
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Dec 24 to Dec 25
$122 total
Dec 24 - Dec 25
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Clean and super close to airport! Great indoor pool area.
Reviewed on Dec 16, 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.
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.
