Windsor Vacations

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Find the Best Windsor Vacation Packages

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
The price is NT$2,047 per night from Sep 1 to Sep 2
NT$2,047
NT$2,359 total
Sep 1 - Sep 2
includes taxes & fees
Red Roof Inn Cleveland - Mentor/ Willoughby
Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

3 out of 5
1715 S Broadway Geneva OH
Fully refundableReserve now, pay when you stay
The price is NT$3,267 per night from Aug 30 to Aug 31
NT$3,267
NT$3,749 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (152 reviews)
"In the stairwell, the is a moldy smell and also a slight odour in the room (but not enough to change room."

Reviewed on 2026/8/6

Wingate by Wyndham Geneva at SPIRE Academy
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
The price is NT$4,041 per night from Aug 9 to Aug 10
NT$4,041
NT$4,637 total
Aug 9 - Aug 10
includes taxes & fees
7.8/10 Good! (313 reviews)
"Lake view was great and the little beach was perfect way to spend the day on the water."

Reviewed on 2026/8/3

Pete's Lakefront Motel
See all 574 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.

Stay near popular Windsor attractions

Windsor Mills Covered Bridge

10.0/10 (3 reviews)
This 1867 Town Lattice truss bridge spans Phelps Creek, surrounded by hardwoods and hemlocks. Drive across this National Historic landmark or photograph its stone abutments during autumn's vibrant display.
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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.