Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Joel Holland

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    Save up to £335 when you book a flight and hotel together*
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Your Windsor Holiday

Lock in a Windsor holiday package and prepare to experience the highlights of this city. Think about staying in the neighbourhood 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 holiday to Windsor today.

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
3,600
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Henry Vilas Zoo, Overture Centre for the Arts and Orpheum Theatre

Our pick of the best 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
Stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
7/10 Good! (888 reviews)
"Good place to stay"

Reviewed on 27 Jun 2025

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
Stay at this 3.5-star luxury hotel in Madison. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (2,742 reviews)
"Great location with a staff focused on customer service. Steve was great with the evening Shuttle. Also appreciated the Governor’s Club level."

Reviewed on 28 Jun 2025

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West
Baymont by Wyndham Madison West/Middleton WI West
2.5 out of 5
8102 Excelsior Dr, Madison, WI
Stay at this family-friendly hotel in Madison. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
7.8/10 Good! (1,005 reviews)
"Clean, Great staff, shower was clogged though"

Reviewed on 26 Jun 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 421 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Windsor travel package cost?
Get your credit card ready, because a trip to Windsor starts from just . When you bundle your flights, hotels and more into a travel package, you'll pick up the best deals.
If I'm not able to travel, can I cancel my Windsor travel package?
You can. We realise even the best-laid plans can go awry, so we're here to help if you have to make changes to your Windsor travel package. You may be able to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Windsor?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities --- we've got them all covered. Choose the combination that best fits you and see your savings grow. We know a package deal is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 properties across the globe, which lets you customize your Windsor adventure.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on the purse strings. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's monthly instalment plans. If paying just a little each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Windsor?
If you're interested in visiting Mousehouse Cheesehaus, give commuting a miss and find a place to stay nearby. It's one of the top attractions in this neighbourhood.
What are the top hotels in Windsor?
Get your holiday off to a great start by booking a room at Motel 6 Madison, WI - East. It's one of most sought-after properties in Windsor. Another option is Hilton Madison Monona Terrace.
How far in advance should I book my Windsor holiday?
Be rewarded with the biggest variety at the cheapest prices by booking your adventure to Windsor early. Air carriers tend to release flight tickets anywhere up to 12 months in advance, so start locking things in as soon as you can. Having said that, Expedia is dedicated to providing you with the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Windsor travel package include?
Car rentals, hotels and flights --- we bring you the best deals. All you have to do is pick your favourite combination. Once you've made your booking, you can add on the exciting stuff like activities and sightseeing tours. Our travel packages make it easy to create an exciting Windsor getaway.
What should I know before booking a Windsor travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and unlock great discounts. Hotels aren't your only choice, however. We've got beach villas, mountain cabins and even houseboats and castles!
Can I choose my airline with a Windsor Expedia travel package?
Yes, and with over 550 airlines to choose from globally, you're not short on choice. Look through the available options and see which airline best fits your budget and needs.

Discover the most popular places to visit in Windsor

University of Wisconsin-Madison

University of Wisconsin-Madison

5/5(2 reviews)

Enjoy the student vibe around University of Wisconsin-Madison, a top university in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison

Alliant Energy Center

Catch an event at Alliant Energy Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Alliant Energy Center

Unmissable things to do in Windsor

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

£24
per adult
Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

£33
per adult
Trolley Pub Public Tour
See all activities in Windsor

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.