Windsor Vacations from $420

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Save 100% on your flight
Price was $588, price is now $420 per person
$420
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
8.8/10 Excellent! (1,004 reviews)
Loved everything about it

Reviewed on Apr 11, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $704, price is now $451 per person
$451
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
9/10 Wonderful! (876 reviews)
Restaurant was amazing

Reviewed on Apr 10, 2026

Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $861, price is now $607 per person
$607
per person
Jul 1 - Jul 6
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Cleveland (CLE)
9.6/10 Exceptional! (713 reviews)
There was no breakfast bar. But the restaurant served breakfast. It was very good but, a little costly.

Reviewed on Apr 16, 2026

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $733, price is now $521 per person
$521
per person
Jul 1 - Jul 6
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Cleveland (CLE)
8.8/10 Excellent! (1,002 reviews)
The restaurant and bar was definitely amazing wife and I enjoyed it Jamie was very kind and a great friend highly recommend. The Schofield was amazing clean and spacious the staff were friendly genuine and great people I had an accident and they went above and beyond to accommodate and remedy the situation. The most professional and best hotel I’ve ever been too definitely recommend premium or better packages as it was an amazing time exceeded expectations!

Reviewed on Apr 15, 2026

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $692, price is now $499 per person
$499
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
7.6/10 Good! (1,028 reviews)
Good service, & good breakfast.

Reviewed on Apr 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windsor
View all trips

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
$62 nightly
The price is $71 total per night from May 13 to May 14
$71 total
May 13 - May 14
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
Our first room smelled horrible. But when I went to the front seat she gave us an up graded room and it was much better. It’s ok for a night but more then that I would look for something a little better.

Reviewed on Apr 15, 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! (1,000 reviews)
The hotel is older but well taken care of. We stayed in the executive room and it was very nice but the 4 poster bed was a bit wobbly. The room was very clean as well as the rest of the hotel. Breakfast was great. The location was close to quite a variety of restaurants. Will stay again when needing ...

Reviewed on Apr 15, 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 29 to Apr 30
$181 total
Apr 29 - Apr 30
Total with taxes and fees
9.2/10 Wonderful! (845 reviews)
Love this place!

Reviewed on Apr 16, 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $420 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.