Windsor Vacations from $470
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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.
Dellshire Resort
Price was $722, price is now $594 per person
$594
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9/10 Wonderful! (514 reviews)
The rooms are spacious and really well decorated. The resort is very new so they are still adding features. I appreciate that everything is well thought out. From the decor to the bath products being made by an indigenous owned company. Definitely will stay again.
Reviewed on Nov 8, 2026
The Madison Concourse Hotel and Governor's Club
Downtown Madison
Price was $577, price is now $531 per person
$531
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9.4/10 Exceptional! (4,264 reviews)
Awesome gym, pool with hot hotub and an amazing sauna that I used every night before bed. The Governor’s club is worth the cost without a doubt. I highly recommend.
Reviewed on Nov 9, 2026
Hyatt Place Madison / Verona
Price was $548, price is now $507 per person
$507
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)
We’ve stayed here before and will stay here again. Reasonable rates, clean property, and nice rooms will keep us coming back.
Reviewed on Nov 9, 2026
Stay near popular Windsor attractions
What to do in Windsor
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
$10
per traveler
100% of travellers recommend
Windsor Hotel Deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $66 total per night from Dec 10 to Dec 11
$66 total
Dec 10 - Dec 11
Total with taxes and fees
7.2/10 Good! (1,010 reviews)
"The facility is undergoing renovations, so be aware of this. If you are price conscious, this facility will meet that need. Staff were very helpful and responsive to inquiries. Highway noise at night can present an intrusion. so opt for rooms away from the highway if you are a light sleeper."
Reviewed on Nov 8, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $146 total per night from Nov 15 to Nov 16
$146 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (4,330 reviews)
"Awesome gym, pool with hot hotub and an amazing sauna that I used every night before bed. The Governor’s club is worth the cost without a doubt. I highly recommend."
Reviewed on Nov 9, 2026
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Fully refundable
$53 nightly
The price is $61 total per night from Dec 4 to Dec 5
$61 total
Dec 4 - Dec 5
Total with taxes and fees
6.2/10 (1,058 reviews)
"Staff was fine, but it’s just a rough place. Only chose this location because it was close to the club downtown we were attending that night. Whole building smelled like weed. Entrance had what looked like bullet proof glass. We were told there was 24 hour security on the premise when we got there. ..."
Reviewed on Nov 9, 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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- Sun Prairie Vacations
- Governor Nelson State Park
- Memorial Union Terrace
- University of Wisconsin Hospital and Clinics
- East Towne Mall
- Wisconsin Historical Museum
- Olbrich Botanical Gardens
- Chazen Museum of Art
- Overture Center for the Arts
- Kohl Center
- State Street Shopping
- Madison Area Technical College
- Monona Vacations
- University of Wisconsin-Madison
- Sun Prairie Family Aquatic Center
- Madison Children's Museum
- Kalahari Indoor Waterpark
- Madison Vacations
- Downtown Madison Vacations
- Washburn Observatory
- Monona Terrace Community and Convention Center
- Lake Mendota
- Tenney Park
- Token Creek Vacations
- Alliant Energy Center
- Camp Randall Stadium
- Lake Monona Shoreline Run
- Wisconsin Dells Vacations
- Wisconsin State Capitol
- Capitol Square
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
