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$2,002 per night from Jan 7 to Jan 8
NT$2,002
NT$2,112 total
includes taxes & fees
Jan 7 - 2025/1/8
7/10 Good! (815 reviews)
"Front desk person was VERY accommodating. Comfortable and super clean room. Quiet - which I needed after a very busy day. Excellent location as well."

Reviewed on 2024/10/28

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
The price is NT$4,547 per night from Jan 5 to Jan 6
NT$4,547
NT$5,252 total
includes taxes & fees
Jan 5 - 2025/1/6
9.4/10 Exceptional! (2,195 reviews)
"Easy access to everything on the square."

Reviewed on 2024/12/24

The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East
DoubleTree by Hilton Madison East
4 out of 5
4402 E Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is NT$3,590 per night from Dec 30 to Dec 31
NT$3,590
NT$4,146 total
includes taxes & fees
Dec 30 - Dec 31
9.2/10 Wonderful! (824 reviews)
"On the road way, yet still quiet quiet and close to interstate"

Reviewed on 2024/12/15

DoubleTree by Hilton Madison East
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

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