Windsor Vacations from $280

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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.
Comfort Suites Twinsburg

Comfort Suites Twinsburg

2.5 out of 5
Price was $370, price is now $280 per person
$280
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (774 reviews)
The property was fair. The room they gave us at first the air conditioning did not work so we had to get another room. The toilet paper holder was broken and the shower curtain had mold on the bottom. Some of the breakfast machines were broken. Overall it was ok.

Reviewed on Aug 18, 2025

The Willoughby House

The Willoughby House

3 out of 5
Save 100% on your flight
Price was $697, price is now $497 per person
$497
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
10/10 Exceptional! (4 reviews)
Clean rooms and comfortable beds helped us throughly enjoy our stay!

Reviewed on Aug 26, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $535, price is now $387 per person
$387
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.6/10 Excellent! (1,034 reviews)
Great location if going to a game or concert - so many drink & dining options in the area & all within walking distance. Hotel was nice & clean! Staff was great too.

Reviewed on Sep 15, 2025

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $680, price is now $495 per person
$495
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (825 reviews)
Clean room | Staff | Bar | Family-friendly

Reviewed on Sep 4, 2025

Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Save 100% on your flight
Price was $491, price is now $373 per person
$373
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (1,002 reviews)
Could’ve been better

Reviewed on Sep 15, 2025

Don't see what you're looking for?
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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
$66 nightly
The price is $77 total per night from Sep 22 to Sep 23
$77 total
Sep 22 - Sep 23
Total with taxes and fees
7.2/10 Good! (1,007 reviews)
Sports
"Room was clean, they did not have soap for you to wash hands in the room though. Staff was friendly and helpful."

Reviewed on Sep 11, 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
$163 nightly
The price is $185 total per night from Oct 13 to Oct 14
$185 total
Oct 13 - Oct 14
Total with taxes and fees
9.2/10 Wonderful! (772 reviews)
"Always a great place to stay. Quiet at night! Sleep well. And close to 'the strip'! : )"

Reviewed on Sep 13, 2025

The Lodge at Geneva
Red Roof Inn Ashtabula - Austinburg

Red Roof Inn Ashtabula - Austinburg

2 out of 5
1860 Austinburg-Ashtabula Rd, I-90 Exit 223, Austinburg, OH
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $80 total per night from Oct 1 to Oct 2
$80 total
Oct 1 - Oct 2
Total with taxes and fees
6.6/10 (854 reviews)
"The room was clean and smelled like it was thoroughly cleaned! One thing that is terrible is the shower gel/shampoo dispenser. It barely provided soap/shampoo. It took more time to get a quarter size of those products than it should."

Reviewed on Sep 15, 2025

Red Roof Inn Ashtabula - Austinburg
See all 544 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $280 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.