Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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 1.852.967 ₫ per night from 27 Aug to 28 Aug
1.852.967 ₫
2.135.544 ₫ total
27 Aug - 28 Aug
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Affordable and we loved our housekeeper Jamie. She was attentive to our needs and very accommodating. Always has a smile and warm friendly greeting. This is our go-to hotel whenever we are in town."

Reviewed on 18 Aug 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
The price is 2.890.155 ₫ per night from 7 Sept to 8 Sept
2.890.155 ₫
3.330.904 ₫ total
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Spacious and clean. Nice to have a living area separate from the bedroom"

Reviewed on 21 Aug 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
The price is 2.348.498 ₫ per night from 26 Aug to 27 Aug
2.348.498 ₫
2.694.842 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8/10 Very Good! (190 reviews)
"By the water"

Reviewed on 18 Aug 2025

Pete's Lakefront Motel
See all 529 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 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.