Windsor Vacation Packages

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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.
Super 8 by Wyndham Madison South

Super 8 by Wyndham Madison South

2.5 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Madison (MSN)
7.2/10 Good! (1,002 reviews)
I normaly get the suite when i stay there and a jacuzzi suite for about $100 go e or take the night cant beat it

Reviewed on Mar. 11, 2025

The Dylin

The Dylin

4 out of 5
Tenney-Lapham
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Madison (MSN)
9.6/10 Exceptional! (14 reviews)
Great location, clean, easy -- really great stay!

Reviewed on Mar. 9, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Save 100% on your flight
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Madison (MSN)
8.4/10 Very Good! (1,004 reviews)
Great place to stay to get the downtown Madison experience.

Reviewed on Mar. 15, 2025

Iron Amethyst Inn Boutique Hotel

Iron Amethyst Inn Boutique Hotel

4 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Madison (MSN)
9.8/10 Exceptional! (54 reviews)
Beautiful, tranquil, historic house. The house was clean & beautifully decorated. They absolutely nailed the Speakeasy, aesthetically & drinks were excellent & reasonable. Would definitely return & recommend.

Reviewed on Nov. 21, 2024

Rodeway Inn

Rodeway Inn

2 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Madison (MSN)
7.6/10 Good! (625 reviews)
It was clean, even while being under construction.

Reviewed on Mar. 15, 2025

Ready to book your vacation to Windsor?

 

Choose your dates

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 CA $85 per night from Apr. 6 to Apr. 7
CA $85
CA $90 total
includes taxes & fees
Apr 6 - Apr 7
7/10 Good! (841 reviews)
Interesting
"Has been an interesting experience. Went to breakfast and the hallway smelled strongly of weed. No plates only bowls, and the gentleman who came to restock had his pants halway down his rear wirh his underwear showing! Not impressive as an employee. Room was fine, plenty of room, lots of pilows, ..."

Reviewed on Mar. 15, 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
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Mar. 30 to Mar. 31
CA $184
CA $213 total
includes taxes & fees
Mar 30 - Mar 31
9.4/10 Exceptional! (2,389 reviews)
"Amaazing hotel"

Reviewed on Mar. 17, 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 CA $156 per night from Mar. 23 to Mar. 24
CA $156
CA $180 total
includes taxes & fees
Mar 23 - Mar 24
9.2/10 Wonderful! (165 reviews)
"Just checked in… room is GREAT!"

Reviewed on Mar. 17, 2025

Moxy Madison Downtown
See all 422 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,199 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

Lake Mendota

Lake Mendota

4.5/5(3 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

CA $45
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

CA $65
per adult
Trolley Pub Public Tour
See all activities in Windsor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.