Windsor Vacations from $278

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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.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
Price was $385, price is now $278 per person
$278
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,389 reviews)
It was very nice and extremely convenient if having an appointment at Cleveland clinic Valet parking is a must if you have appointments scheduled

Reviewed on Jun 15, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $388, price is now $278 per person
$278
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (898 reviews)
Front Desk Team Excelnt Bar and Returant Team did a great Job .

Reviewed on Jun 13, 2026

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Save 100% on your flight
Price was $421, price is now $313 per person
$313
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
The staff, from the front desk to the valet was amazing 👏👏👏 However, the room and the bathroom left a few things to be desired The shower was miserable ( second floor) The carpets were threadbare No way to control the temperatures in the room And the food was another story😓

Reviewed on Jun 12, 2026

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Save 100% on your flight
Price was $690, price is now $525 per person
$525
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (5 reviews)
ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $596, price is now $463 per person
$463
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (744 reviews)
Excellent accommodations.

Reviewed on Jun 16, 2026

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Stay near popular Windsor attractions

Windsor Mills Covered Bridge

10.0/5 (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.
See properties

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
$64 nightly
The price is $74 total per night from Jun 21 to Jun 22
$74 total
Jun 21 - Jun 22
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
"Very pretty property. The room was very nice and more spacious than what I honestly anticipated. The property is very well kept and has really pretty flowers at the entrance. Check in went smoothly and the hotel clerk was very helpful and friendly. Great experience will stay again when our family ..."

Reviewed on Jun 12, 2026

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
$221 nightly
The price is $251 total per night from Jun 21 to Jun 22
$251 total
Jun 21 - Jun 22
Total with taxes and fees
9.2/10 Wonderful! (871 reviews)
"The staff was very courteous and helpful our whole stay"

Reviewed on Jun 15, 2026

The Lodge at Geneva
Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

3 out of 5
1715 S Broadway Geneva OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Jun 21 to Jun 22
$116 total
Jun 21 - Jun 22
Total with taxes and fees
9.2/10 Wonderful! (90 reviews)
"Overnight staff, very clean hotel! The staff extremely friendly!"

Reviewed on Jun 14, 2026

Wingate by Wyndham Geneva at SPIRE Academy
See all 580 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 $278 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.