Windsor Vacations from $378

Book a Hotel + Flight or Car together to unlock savings

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.
Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was $543, price is now $378 per person
$378
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
17.6/10 Exceptional! (1,002 reviews)
It was clean and staff were nice. One suggestion in handicap accessible rooms toilets should be handicap as well. They were too low with nothing to hold on to when lowering yourself.

Reviewed on Nov 15, 2025

Embassy Suites by Hilton Cleveland Rockside

Embassy Suites by Hilton Cleveland Rockside

3.5 out of 5
Price was $621, price is now $454 per person
$454
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
14.8/10 Exceptional! (1,007 reviews)
Extremely friendly staff! Excellent facility all the way around!

Reviewed on Nov 14, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $697, price is now $511 per person
$511
per person
Jan 29 - Feb 2
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
17.6/10 Exceptional! (1,229 reviews)
THE STAFF WAS VERY COURTEOUS MADE YOU FEEL WELCOMED.

Reviewed on Nov 11, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $609, price is now $448 per person
$448
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
17.2/10 Exceptional! (1,013 reviews)
Check in was seamless and the room was lovely

Reviewed on Nov 16, 2025

Hampton Inn Cleveland-Westlake

Hampton Inn Cleveland-Westlake

2.5 out of 5
Price was $548, price is now $410 per person
$410
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
8.2/10 Very Good! (1,011 reviews)
It’s really the staff making this place awesome. Decafs is made at evenings and the skill they put into making omelets are examples of thoughtful effort. Thank you.

Reviewed on Nov 14, 2025

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Discover the most popular places to visit in Windsor

Windsor Mills Covered Bridge

5/5(3 reviews)

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 Nov 20 to Nov 21
$69 total
Nov 20 - Nov 21
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
I had two dogs with me, so being able to step right outside with them when they needed to potty was super convenient.

Reviewed on Nov 11, 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
$125 nightly
The price is $141 total per night from Nov 18 to Nov 19
$141 total
Nov 18 - Nov 19
Total with taxes and fees
9.2/10 Wonderful! (800 reviews)
Vey clean room. Very comfortable. Beautiful grounds. Staff was nice!!!!

Reviewed on Nov 3, 2025

The Lodge at Geneva
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd Painesville OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Nov 23 to Nov 24
$116 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Room clean beds and pillows comfortable. Gym clean but nothing to clean equipment when you finish. Pool looked nice only had issue with no TV their system was down and did not know when it would be up but upon check in nothing was said phone in room did not work either. But overall it was safe and ...

Reviewed on Nov 8, 2025

Comfort Inn
See all 550 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 $378 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.