Windsor Vacations from $433
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Photo by Joel Holland
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.
Christmas Mountain Campground
Price was $554, price is now $433 per person
$433
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (71 reviews)
Great well kept grounds. Missing wash cloths for bathroom. Not to big of a deal and that was the only hiccup. Very comfortable beds!
Reviewed on Oct 19, 2025
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort
Price was $616, price is now $490 per person
$490
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
8.4/10 Very Good! (121 reviews)
All was great and will come back again
Reviewed on Sep 29, 2025
Hilton Madison Monona Terrace
Downtown Madison
Price was $1,010, price is now $821 per person
$821
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Madison (MSN)
8.6/10 Excellent! (1,009 reviews)
There is a fan or compressor cycling which ran all night.
Very little sleep.
Reviewed on Nov 4, 2025
Bluegreen Odyssey Dells
Lake Delton
Price was $589, price is now $496 per person
$496
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
9.4/10 Exceptional! (157 reviews)
I wish they would specify better on which hotel that you are staying at because they have so many I loved the room it was spacious and clean. I communicated with the front desk through text, which was very convenient. The only problem I had was getting lost, trying to get back to my room. I stopped and asked a couple of the workers that was outside of a room looking at videos on a phone she gave me the wrong directions, and I ended back up on the floor that I originally was on. I told her that was not the right way she started being very rude I could not understand what she said her name was because I did ask it sounded like it started with a S she has a accent. I was just asking for help there was no reason to be rude.
Reviewed on Oct 7, 2025
Discover the most popular places to visit in Windsor
University of Wisconsin-Madison
4.5/5(872 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.
Capitol Square
4.5/5(710 reviews)
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
4.5/5(164 reviews)
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
$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
$62 nightly
The price is $65 total per night from Dec 1 to Dec 2
$65 total
Dec 1 - Dec 2
Total with taxes and fees
7/10 Good! (1,001 reviews)
Very average hotel, but I have no big complaints. The workers there were nice and doing the best they could under the circumstances in which they were placed. Being close to a Kwik Trip and a restaurant was a benefit.
Reviewed on Oct 30, 2025
Super 8 by Wyndham Windsor/Madison North
4506 Lake Circle, Windsor, WI
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $81 total per night from Dec 3 to Dec 4
$81 total
Dec 3 - Dec 4
Total with taxes and fees
6.4/10 (481 reviews)
Clean, friendly service
Reviewed on Jun 29, 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 Nov 9 to Nov 10
$161 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (3,257 reviews)
Room was clean, check in and out was simple
Reviewed on Nov 2, 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.