Windsor Vacations from $561

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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 Forsyth

FairBridge Inn Express Decatur Forsyth

2.5 out of 5
Price was $569, price is now $561 per person
$561
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Stillwater (SWO) to Decatur (DEC)
7.2/10 Good! (997 reviews)

Locust housing

Locust housing

2 out of 5
Price was $1,467, price is now $1,286 per person
$1,286
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Stillwater (SWO) to Decatur (DEC)
No reviews

Decatur Conference Center & Hotel

Decatur Conference Center & Hotel

2.5 out of 5
Price was $619, price is now $600 per person
$600
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Stillwater (SWO) to Decatur (DEC)
8/10 Very Good! (1,005 reviews)

Hawthorn Extended Stay by Wyndham Decatur

Hawthorn Extended Stay by Wyndham Decatur

3 out of 5
Price was $578, price is now $571 per person
$571
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Stillwater (SWO) to Decatur (DEC)
7.2/10 Good! (1,004 reviews)

Best Western Forsyth - Decatur

Best Western Forsyth - Decatur

2.5 out of 5
Price was $589, price is now $586 per person
$586
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Stillwater (SWO) to Decatur (DEC)
8/10 Very Good! (1,002 reviews)

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Windsor Hotel Deals

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
$95 nightly
The price is $106 total per night from Dec 3 to Dec 4
$106 total
Dec 3 - Dec 4
Total with taxes and fees
Holiday Inn Express & Suites Mattoon by IHG
Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E Mattoon IL
Fully refundable
$84 nightly
The price is $94 total per night from Nov 26 to Nov 27
$94 total
Nov 26 - Nov 27
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Wonderful room. Very comfortable and spacious. Would definitely stay here again"

Reviewed on Oct 30, 2026

Comfort Suites Mattoon East
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
$85 nightly
The price is $95 total per night from Nov 5 to Nov 6
$95 total
Nov 5 - Nov 6
Total with taxes and fees
8.2/10 Very Good! (650 reviews)
"This is a great little stay in Mattoon. The woman that checked me in was EXTREMELY friendly, energetic and overall pleasant. In our two-day stay we had plenty of interactions. Also, I usually do not care for hotel continental breakfasts and eat them out of convenience or not at all... but the breakfast ..."

Reviewed on Oct 27, 2026

Best Western Heartland Inn
See all 66 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 $561 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.