Windsor Holidays

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    Packages with flights are ATOL protected

Your Windsor Holiday

When a getaway to the city is calling your name, answer it with a Windsor holiday package. With all your travel arrangements under control before you go, all you have to do here is focus on having the time of your life. Fill your trip to Windsor with tours of its big-hitting attractions. First stop? Make a beeline for Wolf Creek State Park. Whoever you're travelling with and whatever your bank balance, your ultimate Windsor holiday is just a few clicks away with Expedia.

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Decatur Airport (DEC)
Population
1,150
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Shelbyville Beach, Wolf Creek State Park and The Little Theatre on the Square

Top hotels in Windsor

Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is £70 per night from 1 Sept to 2 Sept
£70
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (800 reviews)
"Clean"

Reviewed on 25 Aug 2025

Comfort Suites Mattoon East
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 £80 per night from 7 Sept to 8 Sept
£80
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (732 reviews)
"Convenient and friendly. Good complimentary breakfast."

Reviewed on 2 Aug 2025

Holiday Inn Express & Suites Mattoon by IHG
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 £111 per night from 1 Sept to 2 Sept
£111
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (183 reviews)
"It was a very smooth check in process. The staff was excellent from the front desk to the waitresses. Everything was very clean and visually appealing."

Reviewed on 25 Aug 2025

Hilton Garden Inn Mattoon, Il
See all 68 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?
From as low as , you can create your own Windsor package. Simply bundle hotels, flights and rental cars and be rewarded with discounts.
If I'm not able to travel, can I cancel my Windsor travel package?
It's hard to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.
How do I get a cheap travel package to Windsor?
Combine your flights and hotels, add extras such as a rental car or activities, and save with a Windsor travel package. You won't just enjoy awesome discounts on your adventure — you'll have lots of choice at your fingertips too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 properties all over the world. Your affordable holiday starts right here, right now!
Does Expedia offer Book Now, Pay Later Windsor holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fantastic getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying bite-sized amounts each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

What are the top hotels in Windsor?
Get your holiday off to a flying start by staying at Hyatt Regency Chicago. It's one of most popular hotels in Windsor. Another welcoming option is The Godfrey Hotel Chicago.
How far in advance should I book my Windsor holiday?
While not all airlines release ticket prices early, it's usually possible to compare international flights on Expedia up to a year in advance. This is the time you can score some incredible bargains. If you're booking late, there's a chance you could get lucky. Sometimes the cheapest prices appear only weeks before departure.
What does an Expedia Windsor travel package include?
Hotels, flights and rental cars — we've got them all. With Expedia, you can shape your Windsor package just the way you want. All you have to do is figure out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the bigger your savings!
What should I know before booking a Windsor travel package?
When you book your flights, hotels and car rentals together, you'll land fantastic discounts. Whether you're planning a wilderness getaway in a cabin or prefer to stay in a ritzy city hotel, Expedia will make it happen for less.
Can I choose my airline with a Windsor Expedia travel package?
Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 airline partners all over the world, so you have lots of choice when arranging your Windsor adventure.

* 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.