Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

The Lodge at Geneva
The Lodge at Geneva
3.5 out of 5
4888 N. Broadway, Geneva, OH
The price is ₩365,297 per night from Jul 6 to Jul 7
₩365,297
₩439,551 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (702 reviews)
"Great location, lovely place. Surprising given the price that breakfast was not included and was so expensive."

Reviewed on Jul 1, 2025

The Lodge at Geneva
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
The price is ₩85,417 per night from Jul 16 to Jul 17
₩85,417
₩98,229 total
Jul 16 - Jul 17
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"great place to air your dogs"

Reviewed on Jun 30, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Towneplace Suites By Marriott Geneva
Towneplace Suites By Marriott Geneva
3 out of 5
5327 Spire Circle, Geneva, OH
The price is ₩148,902 per night from Jul 13 to Jul 14
₩148,902
₩170,865 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (256 reviews)
"The whole room was great Evan had a little kitchen in the room. Will stay again."

Reviewed on Jul 1, 2025

Towneplace Suites By Marriott Geneva
See all 499 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?
Offering great value package deals 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?
If you're hoping to score a cheap Windsor vacation package, consider planning a trip in January, February and November. You're likely to find lower rates on flights and accommodations during these months --- ideal for a budget-friendly break.
How many days is enough for Windsor?
Generally, a handful of days is enough to tick off the main attractions during your Windsor vacation. However, if you prefer to have more time to unwind or go on day trips, consider extending your itinerary.
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.
How to plan a trip to Windsor?

  1. Choose when to go: Check your schedule and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Windsor.
  2. Set a budget: Factor in costs like flights, meals and transportation when working out how much to put aside for your trip to Windsor. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Decide how long to go away for: Now that you're more familiar with Windsor, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Windsor vacation package.

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