Windsor Vacations from $1,000
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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.
Decatur Conference Center & Hotel
$1,000
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Decatur (DEC)
8/10 Very Good! (1,014 reviews)
The complimentary breakfast was so-so. Biscuits had texture of a hockey puck, no selection of juice, orange only. The only thing good was the sausage and coffee. I enjoy watching TV when I'm traveling. I also enjoy watching FOX News. Unfortunately, the channel for FOX was not available and showed something else entirely. Should I assume that being in a BLUE state, conservative shows are not available? I will say the beds were comfortable and the room was clean.
Reviewed on Sep 2, 2026
Sleep Inn Decatur I-72
$1,052
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Decatur (DEC)
7/10 Good! (521 reviews)
Hair and mold in shower area. Sink area was lose. Tiles falling off in breakfast and lobby areas. Needs to be completely repaired, repainted, and a good cleaning. Would not recommend.
Reviewed on Sep 2, 2026
Best Western Forsyth - Decatur
$1,062
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Decatur (DEC)
8/10 Very Good! (1,006 reviews)
It was nice that the hotel was fairly newer. However, they were things that probably could be fixed easily. A button missing from the elevator, long scratches or cuts on the wall where people have banged in the luggage carrier, and the phone had a broken cord, so it did not work and you cannot call the desk on it. The TV cable was not working and the front desk never sent someone up after saying they would. The bathroom was very small. The toilet kept running during the night. The breakfast was very subpar and was not stocked continuously. The front desk person had to be the one to get something for the breakfast bar, which is difficult in the morning when people are checking out.
Reviewed on Aug 31, 2026
Windsor Hotel Deals
Comfort Suites Mattoon East
1408 Broadway Ave E Mattoon IL
Fully refundable
$88 nightly
$98 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express & Suites Mattoon by IHG
121 Swords Dr Mattoon IL
Fully refundable
$112 nightly
$125 total
Sep 8 - Sep 9
Total with taxes and fees
8.2/10 Very Good! (824 reviews)
"Awesome"
Reviewed on Sep 3, 2026
Quality Inn & Suites Mattoon South
4922 Paradise Rd Mattoon IL
Fully refundable
$88 nightly
$97 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (832 reviews)
"Check out usually is fairly easy. However no one was at the front desk when we wanted to check out and we did wait about five minutes before I just left the unattended room key with other unattended room keys near the desk phone. We tried to dial 0 for assistance as displayed by a sign near a phone ..."
Reviewed on Aug 27, 2026
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 $1,000 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.
