Windsor Vacations from $373
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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.
Hilton Garden Inn Cleveland Downtown
Downtown Cleveland
Save 100% on your flight
Price was $550, price is now $394 per person
$394
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,008 reviews)
Good service, & good breakfast.
Reviewed on Apr 11, 2026
The Westin Cleveland Downtown
Downtown Cleveland
Save 100% on your flight
Price was $1,553, price is now $1,168 per person
$1,168
per person
Jun 25 - Jun 28
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
8.6/10 Excellent! (2,104 reviews)
The gym was very useful, one of the best hotel gyms I've seen
Reviewed on Apr 12, 2026
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 Hotel Deals
Red Roof Inn Cleveland - Mentor/ Willoughby
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $69 total per night from Apr 23 to Apr 24
$69 total
Apr 23 - Apr 24
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
It smelled like roaches, crack, and old carpet! I found USED linen underneath my mattress. I only stayed a few hours. As soon as midnight hit I left and went to another hotel! I wasn’t even concerned with the money I wasted.
Reviewed on Apr 12, 2026
Best Western Plus Mentor-Cleveland Northeast
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! (1,010 reviews)
Clean, shower was great, friendly desk service, quiet, gym was ok, breakfast good, room lighting was a little dim, but overall, wonderful! Thank you! Hope to stay here again.
Reviewed on Apr 12, 2026
The Lodge at Geneva
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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
