Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
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    Better together
    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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.

Windsor Hotel Deals

Best Western Heartland Inn
Best Western Heartland Inn
2.5 out of 5
1416 Broadway Avenue East, Mattoon, IL
The price is CA $115 per night from May 1 to May 2
CA $115
CA $128 total
includes taxes & fees
May 1 - May 2
8.2/10 Very Good! (451 reviews)
"Clean and friendly staff. Breakfast was good. Nice bedding and bed was readonably comfortable. Needed a quick stop that was dog friendly. Great place for the price."

Reviewed on Apr. 13, 2024

Best Western Heartland Inn
Comfort Suites Mattoon
Comfort Suites Mattoon
2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 26 to May 27
CA $134
CA $150 total
includes taxes & fees
May 26 - May 27
8.6/10 Excellent! (541 reviews)
"Clean, quiet an comfortable."

Reviewed on Apr. 14, 2024

Comfort Suites Mattoon
Holiday Inn Express & Suites Mattoon, an IHG Hotel
Holiday Inn Express & Suites Mattoon, an IHG Hotel
2.5 out of 5
121 Swords Dr, Mattoon, IL
Fully refundable
The price is CA $136 per night from May 26 to May 27
CA $136
CA $152 total
includes taxes & fees
May 26 - May 27
8.2/10 Very Good! (645 reviews)
"Front desk staff was very friendly and efficient!"

Reviewed on Apr. 10, 2024

Holiday Inn Express & Suites Mattoon, an IHG Hotel
See all 44 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.

Explore other types of vacation packages

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Frequently asked questions

How much does a Windsor vacation package cost?
We make it easy to travel somewhere new, with Windsor packages starting from as little as . You’ll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Windsor?
Search for flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with a Windsor vacation package. It’s as simple as that! From flights and hotels to tours and rental cars, Expedia is your gateway to cheap travel. And with more than 550 partner airlines and 1,000,000 hotel options across the globe to pick from, you’ll never be short of choice.
How far in advance should I book my Windsor vacation?
Be rewarded with the biggest variety and the lowest prices by booking your vacation to Windsor nice and early. Airlines usually sell flight tickets anywhere up to 12 months before departure, so secure your spot as soon as you can. That being said, Expedia is committed to giving you the best bargains around, so it’s always a good time to book your dream vacation!
What does an Expedia Windsor travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Windsor package that works for you. Heading off for a few weeks? Check out a hotel, flight and rental car bundle. If you’re taking a short break, an airfare and hotel deal could be more your style. Activities can also be added once you’ve made your booking. Our vacation packages make it easy to plan and save.
What should I know before booking a Windsor travel package?
When you book your hotels, flights and car rentals together, you’ll enjoy incredible discounts. Whether you’re planning a mountain getaway in a cabin or would rather stay in a ritzy city hotel, Expedia will make it happen for less.
Can I choose my airline with a Windsor Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just choose the carrier that suits you and craft the perfect Windsor trip.
If I'm not able to travel, can I cancel my Windsor vacation package?
Don’t stress if you’re rethinking your Windsor vacation package — it’s possible to change or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can sometimes throw you a curveball, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’re ready to help.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.