Windsor Vacation Packages & Trips 2025 from CA $1,089

Your Windsor Vacation

Lock in a Windsor vacation package and prepare to experience the highlights of this city. Think about staying in the neighborhood of Marquette, which is good for cycling, culture and fishing. You'll want to go sightseeing during your trip to Windsor. Find time for top attractions such as Pink Elephant, Sun Prairie Golf Course and Token Creek Park. Browse Expedia's extensive range of travel options and book your dream vacation to Windsor today.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hampton Inn & Suites Madison-West

per person

Feb. 13 - Feb. 17

found 23 hours ago

Roundtrip flight included

Kelowna (YLW) to Madison (MSN)

9/10 Wonderful! (1,000 reviews)

2nd stay, but unfortunately, not like the first. Both mornings, SPA has zero heat - known issue (they said) but not fixed - not being picky, but I travel for work and I specifically pick hotels with a Fitness Center and Spa as it is part of my morning work out. Then, unruly guests from 2:30am-3:30am - waking me out of a dead sleep

Reviewed on Dec. 12, 2024

Moxy Madison Downtown

Tenney-Lapham

per person

Feb. 13 - Feb. 17

found 23 hours ago

Roundtrip flight included

Kelowna (YLW) to Madison (MSN)

9/10 Wonderful! (108 reviews)

The staff were incredibly friendly and professional. Facility-wise I wish there'd been a dresser of some sort, and a chair. We had 2 suitcases and only one rack. So one suitcase had to go on the floor.

Reviewed on Dec. 4, 2024

The Dylin by Locale

Tenney-Lapham

per person

Feb. 13 - Feb. 17

found 23 hours ago

Roundtrip flight included

Kelowna (YLW) to Madison (MSN)

No reviews

Days Inn & Suites by Wyndham Madison

per person

Feb. 13 - Feb. 17

found 23 hours ago

Roundtrip flight included

Kelowna (YLW) to Madison (MSN)

8.4/10 Very Good! (1,001 reviews)

Loved my stay here! I was in town for the holiday to see my brothers, i was able to bring my pups and it was a good stay!

Reviewed on Dec. 6, 2024

The Edgewater

Downtown Madison

per person

Feb. 13 - Feb. 17

found 23 hours ago

Roundtrip flight included

Kelowna (YLW) to Madison (MSN)

9.2/10 Wonderful! (1,001 reviews)

Beautiful at Christmas. Highly recommend

Reviewed on Dec. 21, 2024

Ready to book your vacation to Windsor?

Choose your dates

Windsor Hotel Deals

Days Inn by Wyndham Madison NE/Windsor

6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI

Fully refundableReserve now, pay when you stay

CA $87

CA $91 total

includes taxes & fees

Dec 29 - Dec 30

7/10 Good! (828 reviews)

Quiet, clean and comfortable

"We stayed here for about a month while our RV was being repaired. It was clean, comfortable, and the staff was amazing! Everyone was really friendly and helpful. There's an excellent restaurant next door (Rodeside Grill) and it's close to Madison and DeForest."

Reviewed on Dec. 6, 2024

The Madison Concourse Hotel and Governor's Club

1 W Dayton St, Madison, WI

Fully refundableReserve now, pay when you stay

CA $200

CA $231 total

includes taxes & fees

Dec 29 - Dec 30

9.4/10 Exceptional! (2,195 reviews)

"Easy check in, beautiful lake views from the room, excellent governors club amenities and views of the capitol"

Reviewed on Dec. 21, 2024

DoubleTree by Hilton Madison East

4402 E Washington Ave, Madison, WI

Fully refundableReserve now, pay when you stay

CA $157

CA $182 total

includes taxes & fees

Dec 25 - Dec 26

9.2/10 Wonderful! (823 reviews)

"On the road way, yet still quiet quiet and close to interstate"

Reviewed on Dec. 15, 2024

See all 393 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 from CA $1,089 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?

Choose your dates: What you plan to do in Windsor and your favorite season can help you decide when to travel.
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.
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.
Bundle your airfare and accommodations: Once you’ve settled on your trip dates and duration, book the right Windsor vacation package for you.