Windsor Vacations from $296
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.
Landing Apartments near Rivergate Park Area
Cuyahoga Valley
$465
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (10 reviews)
I liked the clean room and the pool but I disliked they gave us the wrong code at first we didn’t check in till about 8:30 because of the run around and I disliked that the elevator was down other than that it was a good stay and I would stay again!!
Reviewed on Aug 24, 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
The Lodge at Geneva-on-the-Lake
4888 North Broadway (SR 534) Geneva-on-the-Lake OH
Fully refundableReserve now, pay when you stay
$176 nightly
$200 total
Oct 1 - Oct 2
Total with taxes and fees
Red Roof Inn Cleveland - Mentor/ Willoughby
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
$62 nightly
$72 total
Oct 1 - Oct 2
Total with taxes and fees
7.2/10 Good! (1,001 reviews)
"I loved my stay"
Reviewed on Aug 29, 2026
Red Roof Inn Ashtabula - Austinburg
1860 Austinburg-Ashtabula Rd Austinburg OH
Fully refundableReserve now, pay when you stay
$74 nightly
$84 total
Sep 20 - Sep 21
Total with taxes and fees
7/10 Good! (1,004 reviews)
"The front desk was not nice he made it uncomfortable and I almost left then. I sent and spend the day with family and later that night I went in and the smell of musty air which got me sick right away. My card did not work to get in and my experience with the front desk earlier in the day made me ..."
Reviewed on Aug 30, 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 $296 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.