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 NT$1,976 per night from Jul 3 to Jul 4
NT$1,976
NT$2,084 total
Jul 3 - Jul 4
includes taxes & fees
7/10 Good! (888 reviews)
"Good place to stay"

Reviewed on 2025/6/27

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! (2,748 reviews)
"Great location, block away from Capitol"

Reviewed on 2025/6/29

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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 NT$1,814 per night from Jul 13 to Jul 14
NT$1,814
NT$2,095 total
Jul 13 - Jul 14
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"Great hotel close to University of Wisconsin campus"

Reviewed on 2025/6/29

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.

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.

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
#springfun beautiful zoo

Henry Vilas Zoo

4.5/5(193 reviews)

Why not see the exotic and native animals who call Henry Vilas Zoo home during your vacation in Madison? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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