Windham Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Windham Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Canton
CA $1,064
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Akron (CAK)
8.4/10 Very good! (1,005 reviews)
O understand that the property is a little dated, but there were several areas on the wall under the heat/air conditioning unit that were quite dirty and had holes in them.
Reviewed on Oct 20, 2026
Holiday Inn Cleveland-Mayfield by IHG
CA $1,051
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
8.8/10 Excellent! (873 reviews)
A staff member entered my room, despite the 'Do not disturb' sign being on the door, and check out is at 12pm. There was no knock, just an immediate entry into my room. I called the front desk and all the girl said was that my room was slated to be cleaned today and that they should have knocked and she is sorry. That is a completely unacceptable response. I could have been unclothed in my room as they entered. I expect better service and communication from a hotel and the violation to my privacy and of my right to stay in the room, that I paid for, until it is time for checkout, and not have a member of staff walk in unannounced is completely unacceptable. Then had the nerve to hide in another room when I opened the door to see who had entered unannounced. I will not stay at this hotel again and would recommend to always use the doorstop, because that is what stopped the person from completely walking into the room on my son and I. Their keycard overrode the additional locking mechanism on the door.
Reviewed on Oct 18, 2026
Ready to book your vacation to Windham?
Windham Hotel Deals
Wingate Suites by Wyndham Youngstown - Austintown
5570 Patriot Blvd Austintown OH
Fully refundableReserve now, pay when you stay
CA $117
CA $135 total
Oct 29 - Oct 30
includes taxes & fees
Kent State University Hotel and Conference Center
215 S. Depeyster Street Kent OH
Fully refundableReserve now, pay when you stay
CA $180
CA $203 total
Nov 19 - Nov 20
includes taxes & fees
Comfort Inn & Suites Cuyahoga Falls - Akron
1420 Main St Cuyahoga Falls OH
Fully refundable
CA $135
CA $156 total
Nov 19 - Nov 20
includes taxes & fees
9/10 Wonderful! (1,035 reviews)
"The looks like it needs remodeling. Floors were lifting and other stuff"
Reviewed on Oct 19, 2026
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.
Frequently asked questions
How much does a Windham vacation package cost?
You'll find cheap prices from CA $865 on Expedia for your Windham break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
If you're looking to snag a cheap Windham vacation package, consider visiting in January, February and November. You'll generally find lower rates on accommodations and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Windham?
The ideal length for your Windham vacation depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to go to all the leading sights and explore some hidden spots along the way.
How to find the best Windham package deals?
Use Expedia's handy filters to help you find some fabulous Windham package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Windham package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Windham vacation as a package?
You can enjoy significant savings on your Windham break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Windham?
If you've got your Windham travel dates confirmed, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Windham?
- Choose when to go: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Windham.
- Set your budget: Consider expenses like flights, transportation and food when working out how much to set aside for your trip to Windham. Then, pick a property that matches your budget, whether that's an economical stay or a swankier retreat.
- Work out your trip length: Consider how long you'd like to spend discovering Windham. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Windham vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
