Windsor Vacations from $288

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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.
Hampton Inn Cleveland-Westlake

Hampton Inn Cleveland-Westlake

2.5 out of 5
Save 100% on your flight
Price was $403, price is now $288 per person
$288
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.2/10 Very Good! (1,001 reviews)
Friendly staff. We just stopped overnight on our way to our destination and did not use the amenities. Bed was comfortable and room clean.

Reviewed on Apr 8, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $655, price is now $438 per person
$438
per person
Jun 26 - Jun 28
found 16 hours ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
9/10 Wonderful! (876 reviews)
All good except the mold/mildew in the shower

Reviewed on Mar 2, 2026

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,018, price is now $688 per person
$688
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.6/10 Excellent! (2,104 reviews)
Clean room! Staff was very kind and attentive. I would recommend!

Reviewed on Apr 8, 2026

The Inn at Fulton

The Inn at Fulton

2 out of 5
Save 100% on your flight
Price was $945, price is now $642 per person
$642
per person
Jun 21 - Jun 24
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
8.2/10 Very Good! (36 reviews)
Looked just like the pictures. Very clean. Only thing i would say is it only had one bathroom and that bathroom is located inside the master room so the other guest had to come in that room to use the bathroom so just be prepared for that. Other than that loved the area and place.

Reviewed on Dec 27, 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 Apr 15 to Apr 16
$69 total
Apr 15 - Apr 16
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
Room needed to be vacuumed better

Reviewed on Apr 6, 2026

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
$101 nightly
The price is $117 total per night from Apr 19 to Apr 20
$117 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Awesome everything very clean. Nice hot water.

Reviewed on Apr 9, 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
$160 nightly
The price is $181 total per night from Apr 27 to Apr 28
$181 total
Apr 27 - Apr 28
Total with taxes and fees
9.2/10 Wonderful! (843 reviews)
We were originally put in a disabled and hearing impaired room, but upon request were moved to a better room. The hotel is not updated at all, carpet was dull and dirty, as well as elevators.

Reviewed on Apr 6, 2026

The Lodge at Geneva
See all 575 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 $288 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.