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 1.847.062 ₫ per night from 19 Aug to 20 Aug
1.847.062 ₫
2.128.739 ₫ total
19 Aug - 20 Aug
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Quick in and out"

Reviewed on 11 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 2.880.944 ₫ per night from 24 Aug to 25 Aug
2.880.944 ₫
3.320.288 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Great place to stay!
"Loved the look of the place. The staff weee all very friendly and helpful The only thing I might do differently is change up the breakfast food with some pancakes or sausage, gravy and biscuits. The scrambled eggs can sometimes get a little moist and no flavor"

Reviewed on 11 Aug 2025

Best Western Plus Mentor-Cleveland Northeast
The Lodge at Geneva

The Lodge at Geneva

3.5 out of 5
4888 N. Broadway, Geneva, OH
Fully refundableReserve now, pay when you stay
The price is 5.228.526 ₫ per night from 14 Sept to 15 Sept
5.228.526 ₫
6.393.778 ₫ total
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (741 reviews)
Spectacular views of Lake
"Town on the Lake just around corner with plenty food options. Great room all the comforts of home. Beautiful views to stroll around the property and enjoy."

Reviewed on 10 Aug 2025

The Lodge at Geneva
See all 527 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.