Windsor Vacations from $1,812

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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.
  • A hotel room with a dining area featuring a round wooden table and chairs, a kitchenette with a coffee machine, and a television mounted on the wall.
    Dec 23 - Dec 28

    FairBridge Inn Express Decatur Forsyth + Flight

    Decatur
    5 nights
    2.5 star property
    7.2/10 - Good (999 reviews)
    Roundtrip • Fairbanks (FAI) - Decatur (DEC)
    FAI - SPI • 2 stops SPI - FAI • 2 stops
    $1,838
    $1,812
    per traveler
    found 1 day ago
    FairBridge Inn Express Decatur Forsyth
  • A two-story house with a front porch, a central door, and two side windows.
    Dec 23 - Dec 28

    Locust housing + Flight

    Decatur
    5 nights
    2.0 star property
    Roundtrip • Fairbanks (FAI) - Decatur (DEC)
    FAI - SPI • 2 stops SPI - FAI • 2 stops
    $4,081
    $3,471
    per traveler
    found 1 day ago
    Locust housing
  • A hotel lobby with a seating area, a fireplace, and a television mounted on the wall.
    Dec 23 - Dec 28

    Decatur Conference Center & Hotel + Flight

    Decatur
    5 nights
    2.5 star property
    8.0/10 - Very good (1,000 reviews)
    "Breakfast was amazing! And the lobby was beautiful"
    Reviewed November 3, 2026
    Roundtrip • Fairbanks (FAI) - Decatur (DEC)
    FAI - SPI • 2 stops SPI - FAI • 2 stops
    $1,950
    $1,898
    per traveler
    found 1 day ago
    Decatur Conference Center & Hotel
  • A hotel entrance with a covered walkway, stone pillars, and a well-maintained lawn.
    Dec 23 - Dec 28

    Holiday Inn & Suites Decatur-Forsyth by IHG + Flight

    Decatur
    5 nights
    3.0 star property
    8.6/10 - Excellent (303 reviews)
    Roundtrip • Fairbanks (FAI) - Decatur (DEC)
    FAI - SPI • 2 stops SPI - FAI • 2 stops
    $1,999
    $1,950
    per traveler
    found 1 day ago
    Holiday Inn & Suites Decatur-Forsyth by IHG
  • Exterior
    Dec 23 - Dec 28

    Garner Hotel Decatur - Forsyth by IHG + Flight

    Decatur
    5 nights
    2.5 star property
    7.8/10 - Good (1,000 reviews)
    "Good location. Cheaper options that are better are out there imo. Clogged glaring with rust. Dirty stained up pull out couches and wall unit air conditioners for a suite room with no circulation upfront to the other guests. Suite room door didn’t have a regular door it had a non privacy glass door so we had to use a sheet over it . I don’t recommend this place . It’s too high, and it’s a bad remodel . Smells like mildew in the bathroom and all the drains didn’t drain properly. It is in a..."
    Reviewed October 19, 2026
    Roundtrip • Fairbanks (FAI) - Decatur (DEC)
    FAI - SPI • 2 stops SPI - FAI • 2 stops
    $1,892
    $1,856
    per traveler
    found 1 day ago
    Garner Hotel Decatur - Forsyth by IHG

Where to stay near Windsor

Windsor offers a delightful blend of outdoor adventures and romantic scenery, perfect for family-friendly vacations. Explore nearby cities like New Windsor and East Windsor, where you’ll find great venues for relaxation and fun. Don’t miss the serene beauty of Windsor Park for a memorable getaway.
A downtown street with historic buildings, benches, and a flag.

Mattoon

Discover Mattoon, a welcoming destination perfectly suited for family travelers and those on a budget who will appreciate its charming mix of outdoor scenery and recreational activities. With attractions like Eastern Illinois University, the historic Lincoln Log Cabin, and the serene Mattoon Peterson Park, visitors can enjoy a variety of experiences. Located about 12 miles from Windsor, Mattoon offers a smart choice for convenient accommodations while exploring the heart of Illinois.

Gays

Ideally situated, Gays offers a fantastic home base for adventure-seeking travelers eager to experience attractions such as Lake Shelbyville and Mattoon Peterson Park. Visitors can enjoy outdoor activities at the lake or relax in the urban park, while also exploring the nearby shopping center and golf options. Located about 6 miles from Windsor, Gays ensures easy access to local highlights, making it a smart choice for your stay. With its blend of family-friendly and budget options, Gays is sure to enhance your vacation experience.

Strasburg

If you are a family traveler, look no further than Strasburg, which features a delightful mix of outdoor adventures and scenic beauty. Enjoy the local attractions, including the serene Lake Shelbyville and the recreational opportunities at Wolf Creek State Park, perfect for creating lasting memories. Located about 6 miles from Windsor, Strasburg makes for an easy getaway while providing a charming atmosphere for relaxation. Choosing Strasburg as your base ensures a wonderful experience filled with nature and fun.

A large lake with a rocky shoreline, surrounded by greenery and trees under a partly cloudy sky.

Shelbyville

Shelbyville stands out as a prime spot for travelers seeking outdoor adventures and scenic beauty. Nestled near Lake Shelbyville, visitors can enjoy activities like swimming at Lake Shelbyville Beach or exploring the nearby national state park. History enthusiasts will appreciate the Shelby County Courthouse, a local landmark. Located about 11 miles from Windsor, Shelbyville offers easy access to these attractions, making it a smart choice for your stay. Experience the charm and recreational opportunities that Shelbyville has to offer!

Allenville

Travelers visiting Windsor will find Allenville to be the ideal base for their vacation, featuring beautiful landscapes and outdoor activities. With attractions like Lake Shelbyville, Wolf Creek State Park, and the modern Mattoon City Hall nearby, Allenville offers a blend of nature and local charm. The village experiences a steady flow of visitors year-round, peaking in May and the summer months. Located about 9 miles from Windsor, Allenville is a smart choice for a memorable stay.

Windsor Hotel Deals

A reception area with a curved counter, a clock, and a sign that reads 'Sole Dreams.'

Suite Dreams Hotel

Suite Dreams Hotel
2.0 star property
13.6 mi from Windsor
7.8 out of 10, Good, (18 reviews)
$76 nightly
The price is $85
Nov 8 - Nov 9
Total with taxes and fees
Suite Dreams Hotel
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.
See all properties in Windsor

Frequently Asked Questions

How much does a Windsor vacation package cost?

You'll find cheap prices from $1,812 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.