Windsor Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Windsor
Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Madison East
€2,679
per person
17 Dec - 21 Dec
found 10 hours ago
Return direct flight included
Dublin (DUB) to Madison (MSN)
9.2/10 Wonderful! (1,000 reviews)
Good location. Breakfast was always running undercooked eggs and our toilet quit working a couple of times and we had to take the cover off and fix.
Reviewed on 1 Oct 2026
The Edgewater
Downtown Madison
€2,766
per person
17 Dec - 21 Dec
found 10 hours ago
Return direct flight included
Dublin (DUB) to Madison (MSN)
9.4/10 Exceptional! (1,008 reviews)
The Edgewater is one of my favorite hotels. I had such a wonderful stay and always enjoy being here. I’ll definitely be back!
Reviewed on 30 Sept 2026
Hotel Ruby Marie
Downtown Madison
€2,731
per person
17 Dec - 21 Dec
found 10 hours ago
Return direct flight included
Dublin (DUB) to Madison (MSN)
9.4/10 Exceptional! (1,006 reviews)
The Up North bar has free drink tickets nightly that are fun for a nightcap.
The included breakfast is great with real eggs and thick bacon is a great way to start the day.
The antique 1920s decor is pretty cool.
Reviewed on 3 Oct 2026
The Madison Concourse Hotel and Governor's Club
Downtown Madison
€2,717
per person
17 Dec - 21 Dec
found 10 hours ago
Return direct flight included
Dublin (DUB) to Madison (MSN)
9.4/10 Exceptional! (4,190 reviews)
Outstanding location and property. My wife and I will be returning for certain!
Reviewed on 2 Oct 2026
Top hotels in Windsor
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
€60
1 Nov - 2 Nov
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
€121
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (4,218 reviews)
"Outstanding location and property. My wife and I will be returning for certain!"
Reviewed on 2 Oct 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
€116
1 Nov - 2 Nov
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Very clean, well maintained, and staffed by genuinely friendly people. Breakfast was included, parking was free, and the complimentary shuttle will take you anywhere within two miles until 10:30 p.m.—perfect for getting to the UW Field House for a women’s volleyball game. The hotel also has a nice ..."
Reviewed on 3 Oct 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
Murmurs of Mourning & Murder: Madison Ghost Tour
€21
per adult
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
€9
per traveller
100% of travellers recommend
Frequently asked questions
How much does a Windsor holiday package cost?
You can snap up a holiday package to this popular destination from €2,679 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?
- Choose your dates: What you plan to do in Windsor and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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.
