Windham Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Quality Lodge

Quality Lodge

2.5 out of 5
Price was CA $1,124, price is now CA $928 per person
CA $928
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
7.8/10 Good! (347 reviews)

Hotel Kilbourne Downtown Sandusky

Hotel Kilbourne Downtown Sandusky

2.5 out of 5
Historic Downtown Sandusky
Price was CA $1,339, price is now CA $1,063 per person
CA $1,063
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
9/10 Wonderful! (708 reviews)
Fun bars

Reviewed on Jul 13, 2026

HomeField Inn.

HomeField Inn.

2 out of 5
Price was CA $1,162, price is now CA $941 per person
CA $941
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.2/10 Very good! (26 reviews)
Property was great. Aside from a few scuffs on the floor, it was pretty clean. Great for the price. Very Helpful staff. Remote Check in was really convenient. Would stay again.

Reviewed on Jul 15, 2026

Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was CA $1,158, price is now CA $962 per person
CA $962
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.8/10 Excellent! (526 reviews)

The Inn at Fulton

The Inn at Fulton

2 out of 5
Price was CA $1,241, price is now CA $1,031 per person
CA $1,031
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.2/10 Very good! (37 reviews)
We would absolutely stay here again. It was a great location close to great restaurant options and pretty views of the downtown and water. In the reviews I read the biggest complaint was the noise level. You could clear as day hear any conversations of other rooms if you were in the hallway. Once inside our rooms it wasn’t as bad but we are pretty easy sleepers and other guests were very respectful.

Reviewed on Mar 21, 2026

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Windham Hotel Deals

Courtyard by Marriott Akron Stow

Courtyard by Marriott Akron Stow

3 out of 5
4047 Bridgewater Pkwy Stow OH
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 19 to Jul 20
CA $167
CA $193 total
Jul 19 - Jul 20
includes taxes & fees
Courtyard by Marriott Akron Stow
Kent State University Hotel and Conference Center

Kent State University Hotel and Conference Center

3.5 out of 5
215 S. Depeyster Street Kent OH
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Aug 2 to Aug 3
CA $170
CA $192 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (1,021 reviews)
"Great stay, clean room And the staff was amazing"

Reviewed on Jul 14, 2026

Kent State University Hotel and Conference Center
Comfort Inn & Suites Cuyahoga Falls - Akron

Comfort Inn & Suites Cuyahoga Falls - Akron

3 out of 5
1420 Main St Cuyahoga Falls OH
Fully refundable
The price is CA $144 per night from Jul 26 to Jul 27
CA $144
CA $166 total
Jul 26 - Jul 27
includes taxes & fees
Comfort Inn & Suites Cuyahoga Falls - Akron
See all 326 properties in Windham
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 Windham vacation package cost?
You'll find cheap prices from CA $928 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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Windham vacation package for you.

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