Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Kitchener (YKF) to Cleveland (CLE)
8.8/10 Excellent! (1,131 reviews)
I didn’t like the parking but everything else was great

Reviewed on Jul. 28, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Kitchener (YKF) to Cleveland (CLE)
8.6/10 Excellent! (1,001 reviews)
Lobby was nice with a bar for evening and served breakfast in the morning. Happy Hour was a nice perk. The hallways had old carpet that didn’t seem clean. The room was small and unimpressive. Had a terrible view.

Reviewed on Jul. 27, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Kitchener (YKF) to Cleveland (CLE)
8.6/10 Excellent! (1,442 reviews)
Nice hotel close to all attractions

Reviewed on Jul. 27, 2025

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Kitchener (YKF) to Cleveland (CLE)
8.4/10 Very Good! (1,194 reviews)
Great location! It’s close to The Rocket Arena, and a number or restaurants and bars. The staff was also very pleasant and helpful

Reviewed on Jul. 28, 2025

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
Downtown Cleveland
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Kitchener (YKF) to Cleveland (CLE)
8.8/10 Excellent! (1,012 reviews)
Amazing place to stay

Reviewed on Jul. 28, 2025

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

Econo Lodge Cleveland Southeast - Kent

Econo Lodge Cleveland Southeast - Kent

2 out of 5
9789 State Route 14, Streetsboro, OH
Fully refundableReserve now, pay when you stay
The price is CA $69 per night from Aug 12 to Aug 13
CA $69
CA $78 total
Aug 12 - Aug 13
includes taxes & fees
7.4/10 Good! (985 reviews)
"location was great! access to stores and restaurants."

Reviewed on Jul. 24, 2025

Econo Lodge Cleveland Southeast - Kent
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
The price is CA $175 per night from Aug 3 to Aug 4
CA $175
CA $197 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,020 reviews)
"great location for the blues festival! Walked to all venues and the area of the hotel was very safe."

Reviewed on Jul. 25, 2025

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 refundableReserve now, pay when you stay
The price is CA $129 per night from Aug 24 to Aug 25
CA $129
CA $149 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"This was a one night stop. First time at Comfort Inn Suites. King room has an attractive layout. Private bedroom from seating area with fold out sofa."

Reviewed on Jul. 21, 2025

Comfort Inn & Suites Cuyahoga Falls - Akron
See all 287 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $1,008 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.

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