Windsor Vacations from $356

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Your Windsor Vacation

When you book a Windsor vacation package, you can relax and enjoy your adventure to the fullest. Uncover the highlights of this fascinating city knowing that all your travel needs have been taken care of before you go. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to start exploring is Windsor Mills Covered Bridge. Don't put off your visit to this destination any longer. The perfect Windsor vacation is a couple of clicks away with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Cedar Stables Inn and Suites
The Willoughby House
The Inn at Fulton
InterContinental Suites Hotel Cleveland by IHG
Sandusky Inn
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Discover the most popular places to visit in Windsor

Windsor Hotel Deals

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

2 out of 5
4166 State Route 306, Willoughby, OH
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $81 total per night from Aug 20 to Aug 21
$81 total
Aug 20 - Aug 21
Total includes taxes and fees
7.2/10 Good! (1,003 reviews)
Great location and friendly staff
"Great location right by the highway exit. Staff was friendly and accommodating. We drove from Cleveland Airport. Friendly staff! :) Keep up the good work! Mentor is a bigger city just 10 minutes away. Great options for restaurants and grocery stores. Too bad they didn't have a mini-fridge in the ..."

Reviewed on Aug 14, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

2.5 out of 5
8434 Mentor Avenue, Mentor, OH
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Aug 24 to Aug 25
$126 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (1,001 reviews)
"Clean, updated, comfortable. Front desk staff friendly and efficient."

Reviewed on Aug 14, 2025

Best Western Plus Mentor-Cleveland Northeast
The Lodge at Geneva

The Lodge at Geneva

3.5 out of 5
4888 N. Broadway, Geneva, OH
$222 nightly
The price is $253 total per night from Sep 1 to Sep 2
$253 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (744 reviews)
"All around"

Reviewed on Aug 14, 2025

The Lodge at Geneva
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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $356 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
November, December and January are the best times to look for cheap Windsor vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Windsor?
With a well-planned itinerary, you can easily hit the most popular Windsor attractions in a few days. But if you want to discover hidden spots or go on day tours, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's filters to help you find some tempting Windsor package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Windsor package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
Secure incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Windsor break.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're like us, you love exploring new places 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 spread the overall 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 great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.