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.
The Edgewater
Downtown Madison
CA $1,037
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (1,007 reviews)
A stay at the Edgewater is always a pleasure, but service in Augies has been disappointing. Disappointing enough to stay at a different hotel. This year was amazingly different. We knew within the first 5 minutes something had changed, and we did see bar staff from last year still worked there. We were greeted with a smile the minute we sat down, the service was fast and friendly and the staff seemed to enjoy being there. They greeted everyone cheerfully and offered recommendations, they were polite and friendly. Great job to everyone on the Augie’s team. We will be back.
Reviewed on Sep 24, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
CA $94
CA $99 total
Oct 11 - Oct 12
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"The man working the front desk was not friendly and when I called on the phone I couldn't even understand what he said when he answered."
Reviewed on Sep 23, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
CA $180
CA $208 total
Oct 26 - Oct 27
includes taxes & fees
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
CA $196
CA $227 total
Oct 11 - Oct 12
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Clean room, good breakfast, not enough parking if you arrive late."
Reviewed on Sep 24, 2026
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.
Stay near popular Windsor attractions
Mousehouse Cheesehaus
9.0/10 (12 reviews)
Enjoy an outing to Mousehouse Cheesehaus during your stay in Windsor. Wander the area's lakeside or simply enjoy one of its top-notch restaurants.
What to do in Windsor
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
CA $15
per traveller
100% of travellers recommend
Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from CA $761 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?
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Windsor vacation package for you.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
