Windsor Vacations from $140

Book a Hotel + Flight or Car together to unlock savings

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.
Wyndham Independence
The Willoughby House
InterContinental Suites Hotel Cleveland by IHG
Kimpton Schofield Hotel by IHG
Hampton Inn & Suites Cleveland/Independence
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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 31 to Sep 1
$81 total
Aug 31 - Sep 1
Total with taxes and fees
7.2/10 Good! (1,008 reviews)
"For a quick stop it's a good place to go"

Reviewed on Aug 22, 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 Sep 1 to Sep 2
$126 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Great place to stay! Very quiet. Clean. The hotel was sold out but would’ve never known. Beds were comfortable. Dave, breakfast host, was very friendly. Breakfast was hot and fresh. Good options. If you’re looking for a modern, cold decor hotel, this is not your place- if you’re looking for a cozy, ..."

Reviewed on Aug 24, 2025

Best Western Plus Mentor-Cleveland Northeast
Pete's Lakefront Motel

Pete's Lakefront Motel

2 out of 5
5225 Old Lake Rd, Geneva, OH
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Aug 26 to Aug 27
$114 total
Aug 26 - Aug 27
Total with taxes and fees
8/10 Very Good! (193 reviews)
"We had to check in at another motel to get a code. No front desk at ours. Air conditioner kept going on and off every 30 seconds. Stated lakeshore view. Yes if we opened the door and went around the corner. The place was ok because we were just staying over night. It was our first time in this area. ..."

Reviewed on Aug 21, 2025

Pete's Lakefront Motel
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 $140 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.