Windsor Vacations from $697
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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.
MainStay Suites Fitchburg - Madison
$706
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
8.8/10 Excellent! (1,003 reviews)
Room clean. Breakfast had hot protein options like eggs, bacon, sausage (huge plus) & Raisin Bran, not just high glycemic carbs like most hotels. Used laundry machines ($5.50 combined for washer & dryer load)—worked OK but jeans still damp in dryer. Coffee, tea, sweeteners & ice water provided in lobby 24/7, nice touch. Elevators slow. Room spacious and bed comfortable. All plumbing & electrical equipment worked. Ample free parking. Not walking distance but short drive to restaurant options. Safe/peaceful area away from the nose-ring/blue-hair/weirdo crowds of downtown & campus and far from street blocking protesters east of downtown.
Reviewed on Oct 6, 2026
Country Inn & Suites by Radisson, Madison Southwest, WI
$730
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
8.6/10 Excellent! (1,004 reviews)
The staff was very rude , and was racist and inconsiderate. We feel they were targeting us although they didn’t kick us out they kept threatening too. They were nice to one of the guest in our room but very rude to the other and the difference was his race.
Reviewed on Oct 9, 2026
Stay near popular Windsor attractions
Mousehouse Cheesehaus
9.0/10 (12 reviews)
Enjoy an outing to Mousehouse Cheesehaus during your stay in Windsor. Wander the area's lakeside or simply enjoy one of its top-notch restaurants.
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
$65 nightly
$68 total
Nov 1 - Nov 2
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
"Hotel had a smell, door wouldn’t close either out a hard push, bathroom tile and call was moldy and stains on the carpet"
Reviewed on Oct 7, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
$161 total
Nov 1 - Nov 2
Total with taxes and fees
The Edgewater
1001 Wisconsin Place Madison WI
Fully refundableReserve now, pay when you stay
$221 nightly
$255 total
Nov 2 - Nov 3
Total with taxes and fees
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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Frequently asked questions
How much does a Windsor vacation package cost?
You can snap up a vacation package to this popular destination from $697 on Expedia. However, how much your vacation to Windsor costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Windsor?
February, November and December are great times to look for cheap Windsor vacation packages. Choosing to travel in quieter periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Windsor?
The ideal length for your Windsor vacation depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to tick off all the leading sights and explore some hidden spots along the way.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Windsor package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor adventure underway.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can customize your Windsor escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you're planning a spontaneous Windsor trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Jet off on your dream getaway to Windsor with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until the next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up cheap deals before they disappear.
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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
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- University of Wisconsin-Madison
- Sun Prairie Family Aquatic Center
- Madison Children's Museum
- Kalahari Indoor Waterpark
- Madison Vacations
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- 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.
