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A wooden covered bridge over a river surrounded by lush greenery.

Windsor Vacations from $321

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windsor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Property amenity
    Sep 10 - Sep 13

    Wyndham Avon + Flight

    Avon
    3 nights
    3.5 star property
    8.8/10 - Excellent (1,039 reviews)
    "."
    Reviewed July 16, 2026
    Roundtrip • Atlanta (ATL) - Cleveland (CLE)
    ATL - CLE • Nonstop CLE - ATL • Nonstop
    $400
    $321
    per traveler
    found 1 day ago
    Wyndham Avon
  • Breakfast, lunch, dinner and brunch served
    Sep 17 - Sep 19

    Fidelity Hotel + Flight

    Downtown Cleveland
    2 nights
    4.5 star property
    9.6/10 - Exceptional (841 reviews)
    Roundtrip • Atlanta (ATL) - Cleveland (CLE)
    ATL - CLE • Nonstop CLE - ATL • Nonstop
    Save 100% on your flight
    $1,032
    $673
    per traveler
    found 13 hours ago
    Fidelity Hotel
  • Standard Apartment (1 Bedroom) | Private kitchen | Coffee/tea maker, fridge, microwave, oven
    Sep 24 - Sep 27

    Landing Apartments near Rivergate Park Area + Flight

    Cuyahoga Valley
    3 nights
    4.0 star property
    9.2/10 - Wonderful (7 reviews)
    "Outstanding views of city from our balcony and fantastic location of condo! We were very pleased with everything about our try here. Definitely would stay here again and recommend it to anyone traveling to the area."
    Reviewed June 29, 2026
    Roundtrip • New York (NYC) - Cleveland (CLE)
    JFK - CLE • Nonstop CLE - JFK • Nonstop
    $921
    $726
    per traveler
    found 18 hours ago
    Landing Apartments near Rivergate Park Area
  • Exterior
    Sep 17 - Sep 19

    InterContinental Cleveland by IHG + Flight

    Fairfax
    2 nights
    4.5 star property
    9.0/10 - Wonderful (915 reviews)
    "Great beds"
    Reviewed July 16, 2026
    Roundtrip • Atlanta (ATL) - Cleveland (CLE)
    ATL - CLE • Nonstop CLE - ATL • Nonstop
    Save 100% on your flight
    $558
    $447
    per traveler
    found 1 day ago
    InterContinental Cleveland by IHG
  • Reception
    Sep 10 - Sep 13

    ROOST Cleveland + Flight

    Downtown Cleveland
    3 nights
    4.0 star property
    9.6/10 - Exceptional (786 reviews)
    Roundtrip • Atlanta (ATL) - Cleveland (CLE)
    ATL - CLE • Nonstop CLE - ATL • Nonstop
    Save 100% on your flight
    $803
    $654
    per traveler
    found 1 day ago
    ROOST Cleveland

Windsor Hotel Deals

Property amenity

Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy
3.0 star property
16.3 mi from Windsor
9.0 out of 10, Wonderful, (127 reviews)
$111 nightly
The price is $127
Jul 30 - Jul 31
Total with taxes and fees
Wingate by Wyndham Geneva at SPIRE Academy
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.
See all properties in Windsor

Frequently Asked Questions

How much does a Windsor vacation package cost?

Offering great value package deals from $321 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.