Windsor Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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 S$104 per night from 21 Jul to 22 Jul
S$104
21 Jul - 22 Jul
includes taxes & fees
7.2/10 Good! (1,008 reviews)
Dog and budget friendly
"Decent dog friendly hotel. Nice staff, comfortable room. Cleanliness could be better, but overall a good place to stop for the night with good price."

Reviewed on 18 Jul, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
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 S$361 per night from 14 Aug to 15 Aug
S$361
14 Aug - 15 Aug
includes taxes & fees
9.2/10 Wonderful! (712 reviews)
Relaxing stay on Lake Erie
"It’s a beautiful property right on the lake with lots of amenities. Pool and shuffle board were our favorites. Our A/C kept us up all night, extremely loud. Maybe needed maintenance. Some issues with waiting for our lunch but was resolved. Fabulous desserts. Breakfast buffet exceptional."

Reviewed on 11 Jul, 2025

The Lodge at Geneva
Towneplace Suites By Marriott Geneva

Towneplace Suites By Marriott Geneva

3 out of 5
5327 Spire Circle, Geneva, OH
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 10 Aug to 11 Aug
S$162
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (271 reviews)
Great stay
"Short overnight stay. The room was great and exactly what we needed."

Reviewed on 16 Jul, 2025

Towneplace Suites By Marriott Geneva
See all 513 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.