Windsor Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 AEDĀ 465 per night from Aug 5 to Aug 6
AEDĀ 465
AEDĀ 536 total
5 Aug - 6 Aug
includes taxes & fees
Best Western Plus Mentor-Cleveland Northeast
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 AEDĀ 406 per night from Jul 30 to Jul 31
AEDĀ 406
AEDĀ 466 total
30 Jul - 31 Jul
includes taxes & fees
9/10 Wonderful! (128 reviews)
"Clean room, friendly staff, good breakfast. Didnā€™t use the pool but Iā€™m sure it is great"

Reviewed on 17 July 2026

Wingate by Wyndham Geneva at SPIRE Academy
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 AEDĀ 236 per night from Aug 2 to Aug 3
AEDĀ 236
AEDĀ 272 total
2 Aug - 3 Aug
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"The front staff person was very kind, friendly, and helpful. I felt safe at this motel. However, the room was filthy and smelled awful. There were stains on the blankets and the bed skirts. The floor felt sticky and grungy to walk in. We accidentally spilled some water and when I used a towel to ..."

Reviewed on 17 July 2026

Red Roof Inn Cleveland - Mentor/ Willoughby
See all 576 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.
See properties

Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Windsor costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Windsor?
If you're looking to book a cheap Windsor vacation package, consider planning a trip in January, February and November. You'll usually find lower prices on airfares and hotels during these months ā€” ideal for a budget-friendly break.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Windsor package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Windsor vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spur-of-the-moment Windsor trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Windsor.
  2. Set your budget: Consider costs such as flights, food and transportation when calculating how much to set aside for your trip to Windsor. Then, select a hotel that works with your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Windsor vacation package.