Windsor Vacations from $328
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Comfort Suites Brunswick - Clevelend Southwest
Price was $704, price is now $570 per person
$570
per person
Apr 1 - Apr 7
found 19 hours ago
Roundtrip flight included
New York (LGA) to Cleveland (CLE)
9.4/10 Exceptional! (518 reviews)
Very clean, had everything we needed. Breakfast included was delicious. Staff was very kind as there was a main water line break in town. They gave us bottles of water while the boil advisory was active.
Reviewed on Jan 25, 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
The Lodge at Geneva
4888 N. Broadway Geneva OH
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $140 total per night from Jan 28 to Jan 29
$140 total
Jan 28 - Jan 29
Total with taxes and fees
9.2/10 Wonderful! (819 reviews)
It was a beautiful resort with a lot to do and a great location
Reviewed on Jan 8, 2026
Red Roof Inn Cleveland - Mentor/ Willoughby
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $65 total per night from Feb 1 to Feb 2
$65 total
Feb 1 - Feb 2
Total with taxes and fees
7.2/10 Good! (1,000 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
Towneplace Suites By Marriott Geneva
5327 Spire Circle Geneva OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Feb 1 to Feb 2
$116 total
Feb 1 - Feb 2
Total with taxes and fees
9.4/10 Exceptional! (376 reviews)
Very clean, wonderful room!
Reviewed on Jan 24, 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 |
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.
