Windsor Vacations from $306

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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.
Embassy Suites by Hilton Cleveland Rockside
Fidelity Hotel
The Westin Cleveland Downtown
Kimpton Schofield Hotel by IHG
Residence Inn By Marriott Cleveland Downtown
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Limited-time deals: Save up to 50% on select hotels.

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
$61 nightly
The price is $70 total per night from Dec 4 to Dec 5
$70 total
Dec 4 - Dec 5
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
I had two dogs with me, so being able to step right outside with them when they needed to potty was super convenient.

Reviewed on Nov 11, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Red Roof Inn Ashtabula - Austinburg

Red Roof Inn Ashtabula - Austinburg

2 out of 5
1860 Austinburg-Ashtabula Rd Austinburg OH
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Dec 3 to Dec 4
$72 total
Dec 3 - Dec 4
Total with taxes and fees
6.8/10 (888 reviews)
Clean rooms. Great staff. Very polite staff at the front desk. Awesome stay!

Reviewed on Nov 24, 2025

Red Roof Inn Ashtabula - Austinburg
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd Painesville OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Dec 28 to Dec 29
$116 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
Clean room ..staff very helpful and friendly .. overall very nice experience . But would recommended more handicap parking spots closer to main entrance

Reviewed on Nov 29, 2025

Comfort Inn
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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Riverdale Road Covered Bridge and Windsor Mills Covered Bridge

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $306 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.