Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Price was CA $1,073, price is now CA $897 per person
CA $897
per person
Oct 10 - Oct 13
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9/10 Wonderful! (1,002 reviews)
Nice hotel! Staff friendly, no issues

Reviewed on Aug. 20, 2025

The Willoughby House

The Willoughby House

3 out of 5
Price was CA $1,182, price is now CA $930 per person
CA $930
per person
Oct 10 - Oct 13
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Beautiful property. Nice location. Excellent lounge & restaurant.

Reviewed on Aug. 4, 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Price was CA $1,256, price is now CA $1,013 per person
CA $1,013
per person
Oct 10 - Oct 13
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
The check in staff were super! Valet was mixed - they charge $25 a day. Out breakfast experience was poor. We arrived w

Reviewed on Aug. 18, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was CA $1,213, price is now CA $990 per person
CA $990
per person
Oct 10 - Oct 13
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (1,153 reviews)
Shuttle to and from Cleveland Clinic. Personnel friendly and helpful. Dining room could add some more options in their menu.Also room service.

Reviewed on Aug. 20, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was CA $1,430, price is now CA $1,193 per person
CA $1,193
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Cleveland (CLE)
8.6/10 Excellent! (1,491 reviews)
Issue w shower water temp adjustment

Reviewed on Aug. 18, 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 $65 per night from Sep 8 to Sep 9
CA $65
CA $73 total
Sep 8 - Sep 9
includes taxes & fees
7.4/10 Good! (1,010 reviews)
"Clean and convenient to Blossom Center. Bare bones, but fine for the price. Could've provided more towels, though Im certain that if I had asked for them, I would've gotten them; just ultimately didn't need them for just two people, barely. Similarly, one more pillow for a king size bed (4 instead ..."

Reviewed on Aug. 19, 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
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Aug 21 to Aug 22
CA $159
CA $179 total
Aug 21 - Aug 22
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"The beds were very comfortable and pillows were grewt. Room was a good size. The bathroom floor was dirty. I do not like that you have to park in the garage across the street and pay $13.50/day. Parking should be included with the room."

Reviewed on Aug. 18, 2025

Kent State University Hotel and Conference Center
The Royal Inn & Suites

The Royal Inn & Suites

2.5 out of 5
2677 Gilchrist Rd, Akron, OH
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 21 to Aug 22
CA $124
CA $142 total
Aug 21 - Aug 22
includes taxes & fees
8.4/10 Very Good! (560 reviews)
Good Value For The Money
"This is a nice locally owned hotel. I was able to speak with one of the owners, and he has a great vision for the hotel. My room was newly remodeled, and the staff was wonderful. I will stay here the next time I'm in town."

Reviewed on Aug. 18, 2025

The Royal Inn & Suites
See all 294 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 $897 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.