Windsor Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Windsor

Comfort Suites Mattoon
Comfort Suites Mattoon
2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 17 Apr to 18 Apr
S$149
includes taxes & fees
17 Apr - 18 Apr
8.6/10 Excellent! (716 reviews)
"Nice rooms good spot"

Reviewed on 19 Mar,2025

Comfort Suites Mattoon
Hilton Garden Inn Mattoon, Il
Hilton Garden Inn Mattoon, Il
3 out of 5
100 Coles Centre Parkway, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is S$201 per night from 6 Apr to 7 Apr
S$201
includes taxes & fees
6 Apr - 7 Apr
8.8/10 Excellent! (151 reviews)
"The staff is the star at this location!! Very friendly and helpful, really above and beyond! The hotel was clean! However, the bathroom kept shutting and it is SMALL!! The bedding is pretty cheap too!! They definitely cut some corners when they built this space!"

Reviewed on 9 Mar,2025

Hilton Garden Inn Mattoon, Il
Holiday Inn Express & Suites Mattoon by IHG
Holiday Inn Express & Suites Mattoon by IHG
2.5 out of 5
121 Swords Dr, Mattoon, IL
Fully refundable
The price is S$183 per night from 10 Apr to 11 Apr
S$183
includes taxes & fees
10 Apr - 11 Apr
8.2/10 Very Good! (701 reviews)
"After paying for my room when I booked it, I was still required to pay an additional $20 on arrival. It would have been nice to have this information ahead of time. However the front desk staff was excellent."

Reviewed on 8 Mar,2025

Holiday Inn Express & Suites Mattoon by IHG
See all 57 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You’ll find cheap prices on Expedia for your Windsor getaway. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and better availability in January, February and November. Explore our cheap Windsor holiday packages and you could get some great off-season discounts.
How many days is enough for Windsor?
With a well-planned schedule, you can easily visit the main Windsor sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Windsor holiday for longer.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and travel dates under our “Packages” tab. Then apply a few filters, like “Property type” and “Guest rating,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with unbeatable savings. If you don’t find the perfect Windsor package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging stays and flights individually. Better still, you can personalise your Windsor trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Windsor?
If you’ve got your Windsor holiday dates locked in, book as soon as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Windsor?

  1. Pick your dates: The things you’d like to do in Windsor and your preferred season will help you decide when to go.
  2. Set a budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Windsor. Then, select a property that matches your budget, whether that’s a wallet-friendly stay or a high-end retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Windsor. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: Once you’ve nailed down your trip dates and duration, lock in the ideal 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.