Windsor Vacations from $541

Book a Hotel + Flight or Car together to unlock savings

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.
Embassy Suites by Hilton Cleveland Rockside

Embassy Suites by Hilton Cleveland Rockside

3.5 out of 5
Save 100% on your flight
Price was $887, price is now $541 per person
$541
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.4/10 Good! (1,011 reviews)
Amazing staff, spacious and clean room.

Reviewed on Nov 8, 2025

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $1,137, price is now $733 per person
$733
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (833 reviews)
I appreciated the gracious and accommodating restaurant staff.

Reviewed on Nov 5, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
Price was $998, price is now $651 per person
$651
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,223 reviews)
The staff were so friendly & helpful.

Reviewed on Nov 6, 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Save 100% on your flight
Price was $1,068, price is now $701 per person
$701
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,005 reviews)
Room was excellent, service was excellent, staff were very nice.

Reviewed on Nov 6, 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 $814, price is now $566 per person
$566
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.6/10 Excellent! (1,014 reviews)
Very nice, clean hotel. Can be a little hetic parking/ using valet w it being on a corner of a busy intersection. But it's downtown and to be expected. Staff were friendly and so accommodating with bringing dogs. I am so use to being put in the "crappy room" when w have the doggo w us but I did not feel that way here. The room was nice, big and updated. Thanks for not just putting us in a outdated dingy room bc we had our pup! Location is good too. We got food from Southern Tier Brewery right around the corner (2 min walk) was excellent but tons of options all around. No need to drive for anything once you are there really can walk to so much right there.

Reviewed on Nov 8, 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
$61 nightly
The price is $70 total per night from Nov 12 to Nov 13
$70 total
Nov 12 - Nov 13
Total with taxes and fees
7.2/10 Good! (1,007 reviews)
Clean room, quiet

Reviewed on Oct 29, 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
$133 nightly
The price is $151 total per night from Nov 10 to Nov 11
$151 total
Nov 10 - Nov 11
Total with taxes and fees
9.2/10 Wonderful! (795 reviews)
The staff was amazing.

Reviewed on Oct 31, 2025

The Lodge at Geneva
Holiday Inn Express & Suites Painesville - Concord by IHG

Holiday Inn Express & Suites Painesville - Concord by IHG

2.5 out of 5
11200 Gold Court, Painesville, OH
Fully refundable
$134 nightly
The price is $154 total per night from Dec 7 to Dec 8
$154 total
Dec 7 - Dec 8
Total with taxes and fees
9.4/10 Exceptional! (862 reviews)
Friendly.staff and clean room

Reviewed on Oct 26, 2025

Holiday Inn Express & Suites Painesville - Concord by IHG
See all 542 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 $541 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.