Windsor Trips (flight + hotel)

    deals illustration
    Better together
    Save up to P 3,118 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Windsor

Suite Dreams Hotel
Suite Dreams Hotel
2.5 out of 5
300 Broadway Avenue East, Mattoon, IL
Fully refundableReserve now, pay when you stay
7.2/10 Good! (473 reviews)
"Great"

Reviewed on Jun 3, 2025

Get rates
Suite Dreams Hotel
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 P5,297 per night from Jun 26 to Jun 27
P5,297
P5,931 total
Jun 26 - Jun 27
includes taxes & fees
8.6/10 Excellent! (757 reviews)
"It was close to a good selection of restaurants and stores. Staff was friendly and welcoming. Area surrounding the hotel is a little "tired" looking and felt sketchy, but the hotel itself was nice and quiet."

Reviewed on Jun 19, 2025

Comfort Suites Mattoon
Quality Inn & Suites
Quality Inn & Suites
2.5 out of 5
4922 Paradise Rd, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is P5,304 per night from Jul 6 to Jul 7
P5,304
P5,887 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (733 reviews)
"Very clean, quiet and relaxing"

Reviewed on Jun 22, 2025

Quality Inn & Suites
See all 65 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.

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices 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 can typically find lower rates and better availability in January, February and November. Explore our cheap Windsor vacation packages and you could get some great off-season discounts.
How many days is enough for Windsor?
With a well-planned schedule, you can easily visit the main Windsor sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Windsor vacation for longer.
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.
How to plan a trip to Windsor?

  1. Pick your dates: The things you'd like to do in Windsor and your preferred season will help you decide when to go.
  2. Set a budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Windsor. Then, select a property that matches your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the ideal Windsor vacation package for you.

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