Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Windsor Vacation

When you book a Windsor vacation package, you can relax and enjoy your adventure to the fullest. Uncover the highlights of this fascinating city knowing that all your travel needs have been taken care of before you go. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to start exploring is Windsor Mills Covered Bridge. Don't put off your visit to this destination any longer. The perfect Windsor vacation is a couple of clicks away with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Cleveland Downtown
Fidelity Hotel
InterContinental Suites Hotel Cleveland by IHG
The Westin Cleveland Downtown
Homewood Suites by Hilton Cleveland-Beachwood

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

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 CA $89 per night from Jun 24 to Jun 25
CA $89
CA $102 total
Jun 24 - Jun 25
includes taxes & fees
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 CA $192 per night from Jun 14 to Jun 15
CA $192
CA $221 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Location was convenient and safe. Hotel was very clean. Beds were comfortable. Breakfast was good. Needs some updating."

Reviewed on May 25, 2026

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 CA $283 per night from Jun 1 to Jun 2
CA $283
CA $345 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (861 reviews)
"Place great views. Beware food at bar shrimp tacos were fried tacos with shell on them and not cleaned"

Reviewed on May 25, 2026

The Lodge at Geneva
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.

Explore a world of travel with Expedia

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