Windsor Vacations from $462

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Mayfield Heights Cleveland East

Comfort Inn Mayfield Heights Cleveland East

2.5 out of 5
Price was $609, price is now $462 per person
$462
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Cleveland (CLE)
8.2/10 Very Good! (1,000 reviews)
Clean room Bathroom Clean Friendly Staff Breakfast Fitness Room

Reviewed on Jan 1, 2026

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
Price was $708, price is now $510 per person
$510
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Cleveland (CLE)
8.8/10 Excellent! (1,231 reviews)
Very reasonable prices and easy to walk to Cleveland Clinic.

Reviewed on Dec 31, 2025

Residence Inn by Marriott Cleveland Beachwood

Residence Inn by Marriott Cleveland Beachwood

3 out of 5
Price was $676, price is now $515 per person
$515
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Cleveland (CLE)
8.6/10 Excellent! (912 reviews)
Breakfast was great. It was quiet and I felt safe

Reviewed on Dec 29, 2025

Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Price was $772, price is now $602 per person
$602
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Cleveland (CLE)
9/10 Wonderful! (1,002 reviews)
The staff were very helpful and accommodating to guest especially the children. They are very welcoming and personable which made them easy to talk to and engage with

Reviewed on Dec 30, 2025

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Discover the most popular places to visit in Windsor

Windsor Mills Covered Bridge

Learn about the local history of Windsor when you take a trip to Windsor Mills Covered Bridge. Experience the area's festivals and entertainment venues.

Windsor Mills Covered Bridge

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
$60 nightly
The price is $69 total per night from Jan 6 to Jan 7
$69 total
Jan 6 - Jan 7
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
A great stay. Room was clean and service was excellent. Thank you

Reviewed on Dec 26, 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
$93 nightly
The price is $107 total per night from Jan 11 to Jan 12
$107 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Clean, well-maintained hotel. Breakfast was not fantastic, but certainly more than adequate. Room was very pleasant. Staff was nice!

Reviewed on Dec 27, 2025

Best Western Plus Mentor-Cleveland Northeast
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd Painesville OH
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $114 total per night from Jan 25 to Jan 26
$114 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Staff was very courteous and helpful.

Reviewed on Dec 23, 2025

Comfort Inn
See all 562 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Riverdale Road Covered Bridge and Windsor Mills Covered Bridge

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $462 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
November, December and January are the best times to look for cheap Windsor vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Windsor?
With a well-planned itinerary, you can easily hit the most popular Windsor attractions in a few days. But if you want to discover hidden spots or go on day tours, think about booking your Windsor vacation for longer.
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 vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation 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 vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Windsor vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.