Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 ￥9,275 per night from Jul 15 to Jul 16
￥9,275
￥9,785 total
Jul 15 - Jul 16
includes taxes & fees
7/10 Good! (897 reviews)
"Certain things could use some maintenance. Was 105 in the pool area."

Reviewed on Jul 7, 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
9.4/10 Exceptional! (2,823 reviews)
"A good place to stay for my one-night overnight in Madison. The staff is super helpful. I was very impressed to learn that when I arrived at the airport too late to catch the hotel’s shuttle, they paid for my cab ride (the hotel apparently has an agreement with certain of the cab companies for this). ..."

Reviewed on Jul 10, 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 ￥10,151 per night from Jul 27 to Jul 28
￥10,151
￥11,724 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,009 reviews)
Good choice if you're in Madison.
"Great place, great rate."

Reviewed on Jul 8, 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 421 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.

Discover the most popular places to visit in Windsor

Cool street art in Madison, Wisconsin

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.

University of Wisconsin-Madison
Capitol Building

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.

Capitol Square
Walks with my nieces!

Lake Mendota

4.5/5(344 reviews)

Commune with nature and explore the great outdoors at Lake Mendota during your travels in Madison. Discover the area's sunsets and shops.

Lake Mendota

What to do in Windsor

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

￥4,629
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

￥6,509
per adult
Trolley Pub Public Tour
Madison: Haunts and Terrors Walking Tour

Madison Ghost Tour: Murmurs of Mourning Murder

￥3,472
per adult
Madison Ghost Tour: Murmurs of Mourning Murder
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this popular destination 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?
January, April and December are the best times to look for cheap Windsor vacation 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 vacation 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 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.
How to plan a trip to Windsor?

  1. Choose your dates: What you plan to do in Windsor and your favorite 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 accommodations: Once you've settled on your trip dates and duration, book the right Windsor vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.