Windsor Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

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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 $90 per night from Aug 24 to Aug 25
CA $90
CA $95 total
Aug 24 - Aug 25
includes taxes & fees
7/10 Good! (929 reviews)
"Right off the interstate. Nice staff"

Reviewed on Aug. 16, 2025

Days Inn by Wyndham Madison NE/Windsor
Super 8 by Wyndham Windsor/Madison North

Super 8 by Wyndham Windsor/Madison North

2 out of 5
4506 Lake Circle, Windsor, WI
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Sep 21 to Sep 22
CA $92
CA $104 total
Sep 21 - Sep 22
includes taxes & fees
6.4/10 (479 reviews)
"Clean, friendly service"

Reviewed on Jun. 29, 2025

Super 8 by Wyndham Windsor/Madison North
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 $174 per night from Aug 31 to Sep 1
CA $174
CA $200 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (2,997 reviews)
"good"

Reviewed on Aug. 18, 2025

The Madison Concourse Hotel and Governor's Club
See all 386 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
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Discover the most popular places to visit in Windsor

Lake Mendota

Lake Mendota

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 $36
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

CA $62
per adult
Trolley Pub Public Tour
The Original Madison Ghost Walk - State Street

The Original Madison Ghost Walk - State Street

CA $41
per adult
100% of travellers recommend
The Original Madison Ghost Walk - State Street
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices on Expedia for your Windsor escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you'd like to book a cheap Windsor vacation package, consider travelling in January, April and December. You're likely to find lower rates on flights and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Windsor?
Generally, a handful of days is enough to explore the top sights during your Windsor vacation. But if you'd like to have some time to unwind or take day tours, think about extending your trip.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Windsor package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor escape by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Windsor?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor break.
How to plan a trip to Windsor?

  1. Choose when to go: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to visit Windsor.
  2. Plan your budget wisely: As well as the cost of your hotel, you should consider other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Windsor.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can work out the perfect length of your break. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Windsor vacation package for you.

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