Windsor Vacation Packages

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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.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Price was CA $1,042, price is now CA $872 per person
CA $872
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.8/10 Excellent! (1,005 reviews)
Great property, very clean, safe. Front desk was nice, Valet was great/ $25 a night, The suite was amazing; 2 double beds in one room, living room/kitchen in the other room, tub and toilet in a separate from sink which makes it easy for everyone to get ready. We went to a concert at the Huntington Bank Field and booked here because the bus is pretty much a straight path there. However, be careful because the bus ride is much longer than we thought, it makes about 15 stops and we waited a while for it to even come. It’s only $5 for the day but we did Uber at one point because we didn’t want to be late. If you aren’t on a time crunch then this hotel is great for fairly close proximity to downtown.

Reviewed on Aug. 24, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was CA $1,222, price is now CA $993 per person
CA $993
per person
Nov 9 - Nov 12
found 23 hours ago
Roundtrip flight included
Halifax (YHZ) to Cleveland (CLE)
8.6/10 Excellent! (1,002 reviews)
The staff at this hotel are amazing! The hotel itself is clean and modern and within walking distance from many attractions. The only “downside” we experienced was an odd loud whirring type noise outside our window at night.

Reviewed on Aug. 23, 2025

The Willoughby House

The Willoughby House

3 out of 5
Price was CA $1,535, price is now CA $1,253 per person
CA $1,253
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Clean rooms and comfortable beds helped us throughly enjoy our stay!

Reviewed on Aug. 26, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was CA $1,344, price is now CA $1,112 per person
CA $1,112
per person
Nov 9 - Nov 12
found 23 hours ago
Roundtrip flight included
Halifax (YHZ) to Cleveland (CLE)
8.6/10 Excellent! (1,512 reviews)
We love Westins... Great room with a view, comfy beds, nice bar and helpful staff.

Reviewed on Aug. 26, 2025

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was CA $1,064, price is now CA $882 per person
CA $882
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Cleveland (CLE)
8.8/10 Excellent! (1,008 reviews)
Everything was amazing

Reviewed on Aug. 24, 2025

Ready to book your vacation to Windsor?

 

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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
The price is CA $87 per night from Sep 1 to Sep 2
CA $87
CA $100 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (1,009 reviews)
"For a quick stop it's a good place to go"

Reviewed on Aug. 22, 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

2.5 out of 5
8434 Mentor Avenue, Mentor, OH
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Sep 7 to Sep 8
CA $151
CA $174 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Great place to stay! Very quiet. Clean. The hotel was sold out but would’ve never known. Beds were comfortable. Dave, breakfast host, was very friendly. Breakfast was hot and fresh. Good options. If you’re looking for a modern, cold decor hotel, this is not your place- if you’re looking for a cozy, ..."

Reviewed on Aug. 24, 2025

Best Western Plus Mentor-Cleveland Northeast
Pete's Lakefront Motel

Pete's Lakefront Motel

2 out of 5
5225 Old Lake Rd, Geneva, OH
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Sep 1 to Sep 2
CA $123
CA $141 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (195 reviews)
"We had to check in at another motel to get a code. No front desk at ours. Air conditioner kept going on and off every 30 seconds. Stated lakeshore view. Yes if we opened the door and went around the corner. The place was ok because we were just staying over night. It was our first time in this area. ..."

Reviewed on Aug. 21, 2025

Pete's Lakefront Motel
See all 531 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this destination from CA $872 on Expedia. But how much your vacation to Windsor costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Windsor?
If you're looking to book a cheap Windsor vacation package, consider planning a trip in January, February and November. You'll usually find lower prices on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Windsor?
With a well-organized travel plan, you can easily visit the main Windsor sights in a few days. But if you want to discover lesser-known spots or go on day tours, consider booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Windsor package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Windsor vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spur-of-the-moment Windsor trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Windsor.
  2. Set your budget: Consider costs such as flights, food and transportation when calculating how much to set aside for your trip to Windsor. Then, select a hotel that works with your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.