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.
ROOST Cleveland
Downtown Cleveland
CA $960
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Cleveland (CLE)
9.6/10 Exceptional! (811 reviews)
It's in a great location for the price. Your cin walking distance to the Rock and Roll Hall of Fame, the ball field, and the Goodtime III narrated your if how Cleveland came about. However, if you decide to park in the hotel garage, there's a daily fee. But you can leave and enter at any time.
Reviewed on Aug 29, 2026
InterContinental Cleveland by IHG
Fairfax
CA $1,489
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Cleveland (CLE)
9/10 Wonderful! (931 reviews)
The hotel was very nice and super convenient while going to Cleveland Clinic. The walkway between the hotel and hospital made things super easy. The front desk staff was professional and friendly. The room was nice, although the bed was a little hard for my liking.
Reviewed on Aug 28, 2026
The Westin Cleveland Downtown
Downtown Cleveland
CA $1,326
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Cleveland (CLE)
8.6/10 Excellent! (248 reviews)
Hotel was very nice, beds were super comfortable would most definitely stay again
Reviewed on Aug 30, 2026
Landing Apartments near Rivergate Park Area
Cuyahoga Valley
CA $1,550
per person
Oct 9 - Oct 12
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Cleveland (CLE)
9.2/10 Wonderful! (9 reviews)
I liked the clean room and the pool but I disliked they gave us the wrong code at first we didn’t check in till about 8:30 because of the run around and I disliked that the elevator was down other than that it was a good stay and I would stay again!!
Reviewed on Aug 24, 2026
Ready to book your vacation to Windham?
Windham Hotel Deals
Kent State University Hotel and Conference Center
215 S. Depeyster Street Kent OH
Fully refundableReserve now, pay when you stay
CA $155
CA $176 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Great location"
Reviewed on Aug 30, 2026
The Aurora - a Boutique Hotel
30 Shawnee Trail Aurora OH
Fully refundableReserve now, pay when you stay
CA $135
CA $152 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (789 reviews)
"Enthusiastic tour, thanks Dayton."
Reviewed on Aug 28, 2026
The Royal Inn & Suites
2677 Gilchrist Rd Akron OH
Fully refundableReserve now, pay when you stay
CA $124
CA $143 total
Aug 31 - Sep 1
includes taxes & fees
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 $960 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.
