Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
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 $87
CA $92 total
Sep 7 - Sep 8
includes taxes & fees
7.2/10 Good! (1,007 reviews)
"The rooms were dated but clean. The shower would not turn off completely. I notified the front desk twice. One front desk person came up and he was also unable to turn it off completely. The breakfast that was offered was something to grab and go. In conclusion, not some place I would stay ..."
Reviewed on Aug 24, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
CA $163
CA $188 total
Sep 6 - Sep 7
includes taxes & fees
9.4/10 Exceptional! (4,123 reviews)
"Loved staying here, the staff were so nice and helpful! The room was comfortable and clean, the amenities were really great and as for location, you can’t find better! Will definitely stay again!"
Reviewed on Aug 25, 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
CA $91
CA $105 total
Sep 20 - Sep 21
includes taxes & fees
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
Murmurs of Mourning & Murder: Madison Ghost Tour
CA $37
per adult
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 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.
