Windsor Holidays

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Top hotels in Windsor

Best Western Heartland Inn

Best Western Heartland Inn

2.5 out of 5
1416 Broadway Avenue East Mattoon IL
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 19 Jul to 20 Jul
S$115
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very good! (611 reviews)
"Great place and good price!"

Reviewed on 11 Jul, 2026

Best Western Heartland Inn
Super 8 by Wyndham Mattoon

Super 8 by Wyndham Mattoon

2 out of 5
205 Mcfall Rd Mattoon IL
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 27 Jul to 28 Jul
S$97
27 Jul - 28 Jul
includes taxes & fees
7.4/10 Good! (729 reviews)
"Well it was not exactly the feeli g of clean and comfortable that I was going for it had stained blankets the floor had stains the shower had no bar to hold my rag the drain fell apart and becsme detached from the tub the shower head fell off the water was really hot I did get burnt when above all ..."

Reviewed on 11 Jul, 2026

Super 8 by Wyndham Mattoon
Quality Inn & Suites Mattoon South

Quality Inn & Suites Mattoon South

2.5 out of 5
4922 Paradise Rd Mattoon IL
Fully refundable
The price is S$141 per night from 5 Aug to 6 Aug
S$141
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (819 reviews)
"Being renovated. Got a newer room"

Reviewed on 12 Jul, 2026

Quality Inn & Suites Mattoon South
See all 65 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.

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.