Windsor Packages (Flight + Hotel)

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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 ฿2,146 per night from 18 Aug to 19 Aug
฿2,146
฿2,473 total
18 Aug - 19 Aug
includes taxes & fees
7.2/10 Good! (1,010 reviews)
"I’m not sure if it was mostly due to humidity or that it is a pet friendly inn but the room had a very bad smell. We needed to go to the store for some room freshener. The floor was sticky. The bath tub was worn. No iron or ironing board. The iron from the office had brown burn on the bottom. Room ..."

Reviewed on 3 Aug 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
The price is ฿4,180 per night from 5 Aug to 6 Aug
฿4,180
฿4,797 total
5 Aug - 6 Aug
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 3 Aug 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 ฿3,579 per night from 30 Aug to 31 Aug
฿3,579
฿4,106 total
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (148 reviews)
"Very clean, great breakfast, and great location. Not too busy Will only stay here when in town."

Reviewed on 3 Aug 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.