Windsor Vacations from $339

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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

Fidelity Hotel

4 out of 5
Downtown Cleveland
Price was $441, price is now $339 per person
$339
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
9.6/10 Exceptional! (425 reviews)
Very nice hotel! Conveniently located closed to everything. Lots of walkable restaurants and bars. Would highly recommend

Reviewed on Oct 23, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $700, price is now $495 per person
$495
per person
Dec 30 - Jan 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Cleveland (CLE)
8.6/10 Excellent! (1,014 reviews)
Pros: The location was walkable and convenient. The front desk and hotel bar staff were very nice. Water was available in the lobby. Cons: A piece of used chewing gum was left in a placard placed on my bed at check in. The front desk staff were kind and extremely apologetic, but it really was one of the grosser things things I’ve encountered at a hotel. The room and amenities are definitely a little dated. I’d recommend parking in one of the nearby garages rather than paying for parking. The PNC Center Garage was great and had cheap event parking the night that I stayed.

Reviewed on Oct 25, 2025

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was $637, price is now $460 per person
$460
per person
Dec 30 - Jan 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Cleveland (CLE)
8.8/10 Excellent! (1,010 reviews)
Clean room, excellent and friendly staff, adequate parking. Could have used an EV charging station in the parking area.

Reviewed on Oct 25, 2025

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $665, price is now $494 per person
$494
per person
Dec 30 - Jan 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Cleveland (CLE)
8.4/10 Very Good! (1,409 reviews)
Perfect location for everything downtown. Clean room and friendly staff

Reviewed on Oct 25, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was $640, price is now $494 per person
$494
per person
Dec 30 - Jan 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Cleveland (CLE)
8.6/10 Excellent! (1,688 reviews)
Very friendly and attentive staff, always available to help and assist. Unfortunately we experienced domestic issues of other guests, who just happened to be above our head which made our night uncomfortable.

Reviewed on Oct 25, 2025

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Discover the most popular places to visit in Windsor

Windsor Mills Covered Bridge

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 Mills Covered Bridge

Windsor Hotel Deals

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

2 out of 5
4166 State Route 306, Willoughby, OH
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $72 total per night from Oct 29 to Oct 30
$72 total
Oct 29 - Oct 30
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Great place for the traveller and great for our short stop over

Reviewed on Oct 22, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
The Lodge at Geneva

The Lodge at Geneva

3.5 out of 5
4888 N. Broadway, Geneva, OH
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $150 total per night from Nov 3 to Nov 4
$150 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (788 reviews)
NA

Reviewed on Oct 14, 2025

The Lodge at Geneva
Comfort Inn

Comfort Inn

2.5 out of 5
7581 Auburn Rd, Rt 44 Off I-90, Painesville, OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Nov 23 to Nov 24
$116 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
Mary was a saint. Helped us settle in after a surgery. Brian was beyond kind and Professional. CC was adorable , sweet, and helpful. Sara was a beautiful woman whose artistic abilities are displayed on the board when you walk into the lobby. We loved our time there. 11 days! Leave tips for Janieth, ...

Reviewed on Oct 24, 2025

Comfort Inn
See all 543 properties in Windsor
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 $339 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.