Windsor Holidays

Photo by Joel Holland

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Top hotels in Windsor

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 S$88 per night from 26 Aug to 27 Aug
S$88
26 Aug - 27 Aug
includes taxes & fees
7/10 Good! (929 reviews)
"Right off the interstate. Nice staff"

Reviewed on 16 Aug, 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 S$96 per night from 21 Sept to 22 Sept
S$96
21 Sept - 22 Sept
includes taxes & fees
6.4/10 (479 reviews)
"Clean, friendly service"

Reviewed on 29 Jun, 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
9.4/10 Exceptional! (2,992 reviews)
"Clean & close to State street."

Reviewed on 19 Aug, 2025

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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.

Popular places to visit

Henry Vilas Zoo

Henry Vilas Zoo

Why not visit the native and exotic animals who call Henry Vilas Zoo home during your travels in Madison? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Henry Vilas Zoo

East Towne Mall

You can enjoy retail therapy at East Towne Mall during your trip to Madison. Savour the lively bars and top-notch restaurants while in town.

East Towne Mall

What to do in Windsor

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

S$33
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

S$58
per adult
Trolley Pub Public Tour
The Original Madison Ghost Walk - State Street

The Original Madison Ghost Walk - State Street

S$39
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 holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday 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 holiday 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can customise 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 holiday 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 favourite 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 accommodation: Once you've settled on your trip dates and duration, book the right Windsor holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.