Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Joel Holland
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    Better together
    Save up to Rp173.195 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Windsor

Days Inn by Wyndham Madison NE/Windsor
Days Inn by Wyndham Madison NE/Windsor
2 out of 5
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Fully refundableReserve now, pay when you stay
The price is Rp1.031.535 per night from 26 Jun to 27 Jun
Rp1.031.535
Rp1.088.269 total
26 Jun - 27 Jun
includes taxes & fees
7/10 Good! (881 reviews)
"Quick easy and comfortable"

Reviewed on 19 Jun 2025

Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club
The Madison Concourse Hotel and Governor's Club
3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (2,724 reviews)
"Love this hotel! Stay here every time we visit our kids in college in Madison!"

Reviewed on 21 Jun 2025

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The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West
Baymont by Wyndham Madison West/Middleton WI West
2.5 out of 5
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is Rp961.684 per night from 30 Jun to 1 Jul
Rp961.684
Rp1.110.745 total
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"Clean and convenient location."

Reviewed on 22 Jun 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 419 properties in Windsor
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.

Frequently asked questions

How much does a Windsor holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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?
January, April and December are the best times to look for cheap Windsor holiday packages. Choosing to travel in less busy months means you'll typically find better prices on flights and hotels.
How many days is enough for Windsor?
The ideal length of your Windsor holiday depends on what you'd like to do. Usually, a few days to a week will give you enough time to tick off all the leading attractions and discover some hidden gems 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Windsor?

  1. Choose your dates: What you plan to do in Windsor and your favourite season can help you decide when to travel.
  2. Set your budget: Consider costs like flights, food and transportation when working out how much to set aside for your trip to Windsor. Then, choose a hotel that suits your budget, whether that's a low-cost stay or a high-end getaway.
  3. Decide your trip length: Consider how long you'd like to spend discovering Windsor. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodation: Once you've settled on your trip dates and duration, book the right Windsor holiday package for you.

Popular places to visit

Alliant Energy Center

Catch an event at Alliant Energy Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Alliant Energy Center

Ho-Chunk Gaming Madison

Why not try your luck with a visit to Ho-Chunk Gaming Madison during your travels in Madison? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Ho-Chunk Gaming Madison

What to do in Windsor

Travel between Chicago O'Hare and Madison

Travel between Chicago O'Hare and Madison

Rp619.697
per adult
Travel between Chicago O'Hare and Madison
Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

Rp390.360
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

Rp734.715
per adult
Trolley Pub Public Tour
See all activities in Windsor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.