Windsor Holidays

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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 Windsor WI
Fully refundableReserve now, pay when you stay
The price is S$93 per night from 15 Jul to 16 Jul
S$93
15 Jul - 16 Jul
includes taxes & fees
7.2/10 Good! (1,006 reviews)
"The hotel was very dirty and had a strong, unpleasant odor throughout. The breakfast area was unclean and not well maintained, making it an unappealing place to eat. The stairwells were covered with spider webs, and there was dirt and grass scattered all the way up and down the stairs. Overall, the ..."

Reviewed on 11 Jul, 2026

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 S$176 per night from 12 Jul to 13 Jul
S$176
12 Jul - 13 Jul
includes taxes & fees
9.4/10 Exceptional! (3,982 reviews)
"It was an amazing experience. Felt like home. I will stay with them again, and again. Highly recommend in my book."

Reviewed on 10 Jul, 2026

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is S$203 per night from 31 Jul to 1 Aug
S$203
31 Jul - 1 Aug
includes taxes & fees
9.2/10 Wonderful! (1,020 reviews)
"Very nice and clean"

Reviewed on 11 Jul, 2026

Best Western Plus InnTowner Madison
See all 410 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.

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.
See properties

What to do in Windsor

Madison Must-See and Must-Eat Locations with Self-Guided Audio Tour

Madison Must-See and Must-Eat Locations with Self-Guided Audio Tour

S$13
per traveller
80% of travellers recommend
Madison Must-See and Must-Eat Locations with Self-Guided Audio Tour
Downtown Madison Sightseeing & History with Self-Guided Audio Tour

Downtown Madison Sightseeing & History with Self-Guided Audio Tour

S$13
per traveller
100% of travellers recommend
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
Murmurs of Mourning & Murder: Madison Ghost Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

S$41
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
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.

Explore a world of travel with Expedia

* 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.