Windsor Holidays

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Top hotels in Windsor

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 Rp1.211.264 per night from 18 Aug to 19 Aug
Rp1.211.264
Rp1.395.981 total
18 Aug - 19 Aug
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"the sheets were clean...only good thing I can say. totally old rundown and dirty motel. would never stay here again."

Reviewed on 29 Jul 2026

Red Roof Inn Cleveland - Mentor/ Willoughby
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 Rp2.260.932 per night from 12 Aug to 13 Aug
Rp2.260.932
Rp2.594.420 total
12 Aug - 13 Aug
includes taxes & fees
7.8/10 Good! (311 reviews)
"Nice clean bathroom. That's important to me"

Reviewed on 31 Jul 2026

Pete's Lakefront Motel
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 Rp1.939.688 per night from 30 Aug to 31 Aug
Rp1.939.688
Rp2.225.792 total
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (142 reviews)
"Good enough for a stopover along the highway."

Reviewed on 29 Jul 2026

Wingate by Wyndham Geneva at SPIRE Academy
See all 572 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 holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday package, consider planning a trip in January, February and November. You're likely to find lower rates on flights and accommodation 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 holiday. 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 holiday package well in advance.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday 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 holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 favourite 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 holiday package.

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