Windsor Vacations from $533

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Your Windsor Vacation

When a getaway to the city is calling your name, answer it with a Windsor vacation 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 traveling with and whatever your bank balance, your ultimate Windsor vacation is just a few clicks away with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
FairBridge Inn express Decatur

FairBridge Inn express Decatur

2.5 out of 5
Price was $625, price is now $533 per person
$533
per person
Apr 5 - Apr 8
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Decatur (DEC)
7/10 Good! (903 reviews)
Breakfast consists of dry cereal the waffle maker toast and biscuits with a plain gravy. Coffee was great they have a coffee maker. Room was clean and didn’t smell like smoke like the hallways do. Thank goodness. Was very happy for the price I paid. I only needed a place to crash was really only there for 6 hrs. Staff was great.

Reviewed on Jan 11, 2026

SureStay by Best Western Forsyth Decatur

SureStay by Best Western Forsyth Decatur

2.5 out of 5
Price was $668, price is now $560 per person
$560
per person
Apr 5 - Apr 8
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Decatur (DEC)
8.2/10 Very Good! (923 reviews)
Clean room, but had to switch rooms because key lock didn’t work. Outside grounds had a lot of garbage and glass around plus old mattresses piled outside the building. Pleasant helpful staff, didn’t have breakfast. Nice enough for the price but with a little cleanup work they would get a much higher rating.

Reviewed on Jan 8, 2026

Decatur Conference Center & Hotel

Decatur Conference Center & Hotel

2.5 out of 5
Price was $735, price is now $620 per person
$620
per person
Apr 5 - Apr 8
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Decatur (DEC)
7.8/10 Good! (933 reviews)
Everything was grade A

Reviewed on Dec 27, 2025

Ramada Limited Decatur

Ramada Limited Decatur

2 out of 5
Price was $642, price is now $541 per person
$541
per person
Apr 5 - Apr 8
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Decatur (DEC)
7/10 Good! (809 reviews)
Location is nice, it’s a nice low key hotel

Reviewed on Sep 7, 2025

Sleep Inn Decatur I-72

Sleep Inn Decatur I-72

2.5 out of 5
Price was $646, price is now $556 per person
$556
per person
Apr 5 - Apr 8
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Decatur (DEC)
7/10 Good! (469 reviews)
The staff was friendly and helpful. Location is great and the price was good.

Reviewed on Oct 7, 2025

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Windsor Hotel Deals

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
$81 nightly
The price is $90 total per night from Jan 25 to Jan 26
$90 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (891 reviews)
Staff at check in was friendly

Reviewed on Jan 10, 2026

Comfort Suites Mattoon East
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
$130 nightly
The price is $145 total per night from Jan 25 to Jan 26
$145 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (213 reviews)
The room was very clean!! We enjoyed our stay and it was quiet. Thank you staff for your help in our stay there. We will be back!! Happy 2026 to all who made us feel at home!! Nice town too. Everything we needed close to us. Great location!!

Reviewed on Jan 6, 2026

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
$97 nightly
The price is $109 total per night from Jan 18 to Jan 19
$109 total
Jan 18 - Jan 19
Total with taxes and fees
8.2/10 Very Good! (759 reviews)
Great stay

Reviewed on Jan 11, 2026

Holiday Inn Express & Suites Mattoon by IHG
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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Decatur Airport (DEC)
Population
1,150
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lake Shelbyville Beach, Wolf Creek State Park and The Little Theatre on the Square

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $533 on Expedia for your Windsor getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Windsor vacation packages and you could score some great off-season discounts.
How many days is enough for Windsor?
Typically, a handful of days is enough to explore the main sights during your Windsor vacation. But if you want to have more time to rest or go on day tours, think about extending your trip.
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 vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights individually. Better still, you can personalize 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 vacation package to Windsor?
If you've got your Windsor vacation 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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Windsor vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.