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 Rp1.581.299 per night from 26 Jul to 27 Jul
Rp1.581.299
Rp1.770.738 total
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very good! (616 reviews)
"The property was clean and staff friendly. My problem was the water didn’t get hot for the shower, everything in my room was leaning and the drawer to the chest wouldn’t stay closed."

Reviewed on 20 Jul 2026

Best Western Heartland Inn
Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E Mattoon IL
Fully refundable
The price is Rp1.657.323 per night from 13 Aug to 14 Aug
Rp1.657.323
Rp1.855.871 total
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (984 reviews)
"I have stayed here before, and have overall found it to be a great place. However, I couldn’t get WiFi, and television reception was not good."

Reviewed on 22 Jul 2026

Comfort Suites Mattoon East
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 Rp1.201.179 per night from 29 Jul to 30 Jul
Rp1.201.179
Rp1.345.081 total
29 Jul - 30 Jul
includes taxes & fees
Super 8 by Wyndham Mattoon
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.