Windsor Vacations from $437

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.
Extended Stay America Suites Cleveland Airport North Olmsted

Extended Stay America Suites Cleveland Airport North Olmsted

2.5 out of 5
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
6.8/10 (869 reviews)
No hot water but it was a hot day anyway, so I didn’t mind.

Reviewed on Jun 25, 2025

Homewood Suites by Hilton Cleveland/Sheffield

Homewood Suites by Hilton Cleveland/Sheffield

3 out of 5
Sheffield
per person
Aug 3 - Aug 8
found 12 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
8.8/10 Excellent! (796 reviews)
Our room waa beautiful. Full refrigerator and dishwasher, stove and microwave. Thexstaff were very friendly.

Reviewed on Jun 14, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
8.6/10 Excellent! (1,399 reviews)
Staff was super friendly and our room was ready prior to checking.

Reviewed on Jul 1, 2025

Hilton Garden Inn Cleveland/Twinsburg

Hilton Garden Inn Cleveland/Twinsburg

3 out of 5
per person
Aug 3 - Aug 8
found 7 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
8.8/10 Excellent! (697 reviews)
Other than waiting 15 minutes for someone to greet me at the front desk it has been a good stay.

Reviewed on Jun 29, 2025

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

2.5 out of 5
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
9.2/10 Wonderful! (1,002 reviews)
Hotel was very dated. Charged a high price for Red Roof quality.

Reviewed on Jun 30, 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

The Lodge at Geneva
The Lodge at Geneva
3.5 out of 5
4888 N. Broadway, Geneva, OH
$284 nightly
The price is $324 total per night from Jul 6 to Jul 7
$324 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (702 reviews)
"Great location, lovely place. Surprising given the price that breakfast was not included and was so expensive."

Reviewed on Jul 1, 2025

The Lodge at Geneva
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
$70 nightly
The price is $81 total per night from Jul 6 to Jul 7
$81 total
Jul 6 - Jul 7
Total includes taxes and fees
7.2/10 Good! (1,002 reviews)
"great place to air your dogs"

Reviewed on Jun 30, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Towneplace Suites By Marriott Geneva
Towneplace Suites By Marriott Geneva
3 out of 5
5327 Spire Circle, Geneva, OH
$110 nightly
The price is $126 total per night from Jul 13 to Jul 14
$126 total
Jul 13 - Jul 14
Total includes taxes and fees
9.4/10 Exceptional! (256 reviews)
"The whole room was great Evan had a little kitchen in the room. Will stay again."

Reviewed on Jul 1, 2025

Towneplace Suites By Marriott Geneva
See all 499 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 $437 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.