Windsor Vacations from $247
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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.
Cedar Stables Inn and Suites
$247
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (549 reviews)
Everyone was so nice and helpful EXCEPT our server at the restaurant!!!! The absolute worst service I’ve EVER had!!!!!! We waited an hour our food!! Server was so rude!
Reviewed on Aug 8, 2026
Highlander Inn Cleveland Beachwood Near I-480
$261
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
5/10 (12 reviews)
The property was poorly maintained. The hall carpets, and the carpets on the stairs were ripped. They were broken tiles in the bathroom. The place looked like it hadn’t been painted since the great depression. This place is a dump.
Reviewed on Aug 7, 2026
ROOST Cleveland
Downtown Cleveland
$397
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (794 reviews)
The Roost was a wonderful place to stay for a fun weekend in downtown Cleveland. The garage was easy to use with the QR code on my phone. The staff person at the desk in the lobby was extremely friendly and helpful. The building was very clean. The 2 bedroom apartment was clean, comfortable and quiet. Ww will definitely return when we are visiting Cleveland.
Reviewed on Aug 9, 2026
Stay near popular Windsor attractions
Windsor Mills Covered Bridge
10.0/10 (3 reviews)
This 1867 Town Lattice truss bridge spans Phelps Creek, surrounded by hardwoods and hemlocks. Drive across this National Historic landmark or photograph its stone abutments during autumn's vibrant display.
Windsor Hotel Deals
Red Roof Inn Cleveland - Mentor/ Willoughby
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
$63 nightly
$73 total
Aug 18 - Aug 19
Total with taxes and fees
Wingate by Wyndham Geneva at SPIRE Academy
1715 S Broadway Geneva OH
Fully refundableReserve now, pay when you stay
$101 nightly
$116 total
Aug 30 - Aug 31
Total with taxes and fees
Pete's Lakefront Motel
5225 Old Lake Rd Geneva OH
Fully refundableReserve now, pay when you stay
$108 nightly
$124 total
Aug 18 - Aug 19
Total with taxes and fees
7.8/10 Good! (321 reviews)
"CLEAN, EASY AND LAKE FRONT"
Reviewed on Aug 10, 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
How much does a Windsor vacation package cost?
Offering great value package deals from $247 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.
