Windsor Vacations from $617
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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.
Club Wyndham Tamarack
$617
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.4/10 Exceptional! (24 reviews)
The room was spotless and it was nice to relax with the fireplace. Also enjoyed saving money by buying and cooking our own meals.
Reviewed on May 12, 2026
Dellshire Resort
$1,086
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (232 reviews)
Dellshire was beautiful, staff was helpful but they can be a little more welcoming. Coming from a background hotel, I believe the first impression means a lot and the staff needed more enthusiastic in the first interaction.
Pool was really nice and the staff working in there was good. I was there for 5 days and I love the breakfast it’s a must!
Parking was amazing being free and lots of space to park.
Overall it was okay.
Reviewed on Aug 8, 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
Murmurs of Mourning & Murder: Madison Ghost Tour
$26
per adult
Windsor Hotel Deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
$63 nightly
$66 total
Sep 7 - Sep 8
Total with taxes and fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
$140 nightly
$162 total
Aug 9 - Aug 10
Total with taxes and fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
$60 nightly
$69 total
Aug 24 - Aug 25
Total with taxes and fees
8/10 Very Good! (1,416 reviews)
"The entrance of the hotel reeked of marijuana, and our room smelled terribly—resembling uncleaned waste masked by a ton of air freshener, creating an unpleasant scent of flowery poop. The property had an overall rundown appearance, featuring nasty carpets and stains on the mattress. Located 30 minutes ..."
Reviewed on Aug 7, 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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Frequently asked questions
How much does a Windsor vacation package cost?
You can snap up a vacation package to this popular destination from $617 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
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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.
