Windsor Vacations from $300

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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.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $382, price is now $300 per person
$300
per person
May 23 - May 25
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
8.8/10 Excellent! (1,231 reviews)
very clean. very nice staff

Reviewed on Mar 2, 2026

The Inn at Fulton

The Inn at Fulton

2 out of 5
Save 100% on your flight
Price was $977, price is now $666 per person
$666
per person
May 22 - May 25
found 20 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
8/10 Very Good! (33 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

The Washington Boutique Hotel

The Washington Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,414, price is now $981 per person
$981
per person
May 22 - May 25
found 20 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
9/10 Wonderful! (80 reviews)
Cute house, neat location. Avoid the crazy neighbor.

Reviewed on Oct 19, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $432, price is now $328 per person
$328
per person
May 23 - May 25
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
8.6/10 Excellent! (1,006 reviews)
Amazing hotel in a great spot. Walking distance to rocket arena and great restaurants. Super clean and friendly staff

Reviewed on Mar 1, 2026

Anchor Bay Inn and Suites

Anchor Bay Inn and Suites

2 out of 5
Price was $557, price is now $438 per person
$438
per person
May 22 - May 25
found 20 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
8.8/10 Excellent! (160 reviews)
Room was very clean but the heat/

Reviewed on Oct 29, 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

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
$98 nightly
The price is $112 total per night from Mar 15 to Mar 16
$112 total
Mar 15 - Mar 16
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Room was magnicent. Staff was great

Reviewed on Feb 21, 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
$123 nightly
The price is $140 total per night from Mar 4 to Mar 5
$140 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (828 reviews)
One of our most favorite parts about staying at hotels is getting to enjoy free continental breakfasts and free coffee all day long. So, of course, we excitedly woke up the kids and rushed downstairs to go and enjoy the morning with a delicious breakfast. To our dismay, we discovered that breakfast ...

Reviewed on Mar 1, 2026

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
$55 nightly
The price is $64 total per night from Mar 8 to Mar 9
$64 total
Mar 8 - Mar 9
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
The staff were good. It served our needs. Our only complaint was that it was supposed to be a non smoking room and it smelled of smoke so badly I did not have a good night's sleep

Reviewed on Feb 25, 2026

Red Roof Inn Cleveland - Mentor/ Willoughby
See all 561 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 $300 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.