Windsor Vacations from $231
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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.
Fidelity Hotel
Downtown Cleveland
$355
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (967 reviews)
Clean room, helpful staff. Next door parking lot was unaffiliated with the hotel and not super convenient to bring luggage in.
Reviewed on Sep 26, 2026
Landing Apartments near Rivergate Park Area
Cuyahoga Valley
$371
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (10 reviews)
Clean and brand new pet friendly apartment in a safe neighborhood. Also has a nice pool.
Reviewed on Sep 8, 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
Best Western Plus Mentor-Cleveland Northeast
8434 Mentor Avenue Mentor OH
Fully refundableReserve now, pay when you stay
$110 nightly
$126 total
Oct 4 - Oct 5
Total with taxes and fees
The Lodge at Geneva-on-the-Lake
4888 North Broadway (SR 534) Geneva-on-the-Lake OH
Fully refundableReserve now, pay when you stay
$141 nightly
$160 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (965 reviews)
"Love the view! Food was good but not great. Coffee ok, appreciate the real half and half cream."
Reviewed on Sep 26, 2026
Pete's Lakefront Motel
5225 Old Lake Rd Geneva OH
Fully refundableReserve now, pay when you stay
$136 nightly
$156 total
Oct 17 - Oct 18
Total with taxes and fees
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 $231 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.
