Windsor Vacations from $656

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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 $712, price is now $656 per person
$656
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Richmond (RIC) 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

Locust housing

Locust housing

2 out of 5
Price was $1,629, price is now $1,453 per person
$1,453
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Richmond (RIC) to Decatur (DEC)
No reviews
Decatur Conference Center & Hotel

Decatur Conference Center & Hotel

2.5 out of 5
Price was $795, price is now $714 per person
$714
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Richmond (RIC) to Decatur (DEC)
7.8/10 Good! (933 reviews)
plentiful breakfast. the girl that checked us in was very professional and welcoming.

Reviewed on Jan 20, 2026

Sleep Inn Decatur I-72

Sleep Inn Decatur I-72

2.5 out of 5
Price was $743, price is now $676 per person
$676
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Richmond (RIC) 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

Quality Inn near I-72 and Hwy 51

Quality Inn near I-72 and Hwy 51

2.5 out of 5
Price was $724, price is now $664 per person
$664
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Richmond (RIC) to Decatur (DEC)
6.8/10 (345 reviews)
This was an “ok” place to lay your head. Friendly staff and comfortable bed. Pillows were disappointing though. We had to ask for our room to be vacuumed. Breakfast was not visually appealing so we did not eat there. The biscuits and gravy had a brown film on top from not being stirred/attended to. That was the only protein offered. Coffee was good. Over all, not horrible but ok for a cheap stay

Reviewed on Dec 14, 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
$82 nightly
The price is $92 total per night from Feb 8 to Feb 9
$92 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (898 reviews)
Clean room, nice staff. Nice breakfast.

Reviewed on Jan 19, 2026

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
$97 nightly
The price is $109 total per night from Feb 4 to Feb 5
$109 total
Feb 4 - Feb 5
Total with taxes and fees
8.2/10 Very Good! (762 reviews)
Nice

Reviewed on Jan 12, 2026

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
$130 nightly
The price is $145 total per night from Feb 6 to Feb 7
$145 total
Feb 6 - Feb 7
Total with taxes and fees
8.8/10 Excellent! (215 reviews)
Great hotel with a pool, fitness center, bar and restaurant.

Reviewed on Jan 19, 2026

Hilton Garden Inn Mattoon, Il
See all 98 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 $656 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.