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 AED 225 per night from Apr 23 to Apr 24
AED 225
AED 237 total
includes taxes & fees
23 Apr - 24 Apr
7/10 Good! (852 reviews)
"very clean and neat, unlike other places we have stayed in Madison area."

Reviewed on 16 April 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
The price is AED 547 per night from Apr 21 to Apr 22
AED 547
AED 632 total
includes taxes & fees
21 Apr - 22 Apr
9.4/10 Exceptional! (2,504 reviews)
"We were in town for cheese con and this hotel was perfect. Highly recommend the governor’s club."

Reviewed on 18 April 2025

The Madison Concourse Hotel and Governor's Club
Moxy Madison Downtown
Moxy Madison Downtown
3.5 out of 5
823 East Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AED 474 per night from Apr 21 to Apr 22
AED 474
AED 547 total
includes taxes & fees
21 Apr - 22 Apr
9/10 Wonderful! (202 reviews)
"We loved the Moxy Hotel , starting from the staff and services, the finest decorations, clean and safe, great location, comfy beds. Love to stay there again when we're back in town."

Reviewed on 17 April 2025

Moxy Madison Downtown
See all 424 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 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
Great place to check out the sunset and hang out with friends and family!

Monona Terrace Community and Convention Center

4.5/5(164 reviews)

Learn about the events happening at Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Monona Terrace Community and Convention Center
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