Windsor Vacations from $179
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.
Holiday Inn Youngstown South by IHG
Price was $239, price is now $179 per person
$179
per person
Feb 20 - Feb 22
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Youngstown (YNG)
8.6/10 Excellent! (635 reviews)
All around great hotel. Pool and hot tub looks good, but I did norht have a minute to jump in. Dining options at the hotel really cover all the bases and the bar there is a great option for some drinks. Hotel itself is a great location in Boardman. Movie theatre, some shopping, restraunts, and bars within walking distance or many mort within a short driving range if you prefer.
Reviewed on Jan 8, 2026
Hampton Inn & Suites Cleveland-Beachwood
Price was $754, price is now $590 per person
$590
per person
Feb 8 - Feb 13
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
9/10 Wonderful! (1,002 reviews)
Staff was great during check in. Room was clean. Haven't used the amenities yet.
Reviewed on Jan 4, 2026
Comfort Inn Mayfield Heights Cleveland East
Price was $546, price is now $443 per person
$443
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
8.2/10 Very Good! (1,000 reviews)
Totally a perfect stay & location esp if you are staying for a number of days.
Reviewed on Jan 8, 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 Jan 13 to Jan 14
$69 total
Jan 13 - Jan 14
Total with taxes and fees
7.2/10 Good! (1,005 reviews)
They do still need to work on locks on door. First door key given didn’t work. Bathroom floor could have used a touch more love. Other than that all was fine.
Reviewed on Dec 31, 2025
Best Western Plus Mentor-Cleveland Northeast
8434 Mentor Avenue Mentor OH
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Jan 20 to Jan 21
$107 total
Jan 20 - Jan 21
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Everything was clean and well kept. Everyone was polite and helpful. Quiet!
Reviewed on Jan 3, 2026
Comfort Inn
7581 Auburn Rd Painesville OH
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $114 total per night from Jan 25 to Jan 26
$114 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Staff was very courteous and helpful.
Reviewed on Dec 23, 2025
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
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.