Windsor Vacations from $475

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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.
The Washington Boutique Hotel

The Washington Boutique Hotel

3 out of 5
Price was $589, price is now $475 per person
$475
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
9/10 Wonderful! (80 reviews)
Cute house, neat location. Avoid the crazy neighbor.

Reviewed on Oct 19, 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 $757, price is now $560 per person
$560
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
8.6/10 Excellent! (1,006 reviews)
The hotel is very pretty but it took the room hours to heat up! The front desk was very accommodating they offered to move me and housekeeping brought extra blankets/comforters and breakfast vouchers were given too us! The problem with the blankets they smelled very bad!

Reviewed on Jan 26, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $883, price is now $674 per person
$674
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
9/10 Wonderful! (843 reviews)
Nice room, restaurants on site and convenient to Cleveland Clinic! Highly recommended!

Reviewed on Jan 20, 2026

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $663, price is now $530 per person
$530
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
8.8/10 Excellent! (1,231 reviews)
The room was very nice and the most of staff courteous.

Reviewed on Jan 25, 2026

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Price was $691, price is now $556 per person
$556
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
8.8/10 Excellent! (1,002 reviews)
The mattress was very hard and the room was hot!

Reviewed on Jan 21, 2026

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Discover the most popular places to visit in Windsor

Windsor Mills Covered Bridge

5/5(3 reviews)

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

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
$122 nightly
The price is $138 total per night from Feb 16 to Feb 17
$138 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (819 reviews)
It was a beautiful resort with a lot to do and a great location

Reviewed on Jan 8, 2026

The Lodge at Geneva
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
$57 nightly
The price is $65 total per night from Feb 1 to Feb 2
$65 total
Feb 1 - Feb 2
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
They do still need to work on locks on door. First door key given didn’t work. Bathroom floor could have used a touch more love. Other than that all was fine.

Reviewed on Dec 31, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Towneplace Suites By Marriott Geneva

Towneplace Suites By Marriott Geneva

3 out of 5
5327 Spire Circle Geneva OH
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Jan 29 to Jan 30
$107 total
Jan 29 - Jan 30
Total with taxes and fees
9.4/10 Exceptional! (376 reviews)
Very clean, wonderful room!

Reviewed on Jan 24, 2026

Towneplace Suites By Marriott Geneva
See all 558 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 $475 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.