Windham Vacations from $438

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windham vacation packages

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

Hampton Inn Cleveland-Westlake

2.5 out of 5
Save 100% on your flight
Price was $594, price is now $438 per person
$438
per person
Jun 11 - Jun 15
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.2/10 Very Good! (1,004 reviews)
It was a good experience. The rooms were a bit small and the breakfast was very busy, but the staff was super friendly and helpful.

Reviewed on May 4, 2026

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $737, price is now $510 per person
$510
per person
Jun 11 - Jun 15
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,008 reviews)
The location was perfect, only 8min walk from the Arena and Stadium

Reviewed on May 3, 2026

Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $797, price is now $558 per person
$558
per person
Jun 11 - Jun 15
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (725 reviews)
Great staff!! And food and drinks were amazing

Reviewed on May 7, 2026

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $857, price is now $615 per person
$615
per person
Jun 11 - Jun 15
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
Cool hotel,in great part of town😁staff was great

Reviewed on May 5, 2026

Comfort Suites Hartville - North Canton

Comfort Suites Hartville - North Canton

2.5 out of 5
Price was $891, price is now $659 per person
$659
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
9.6/10 Exceptional! (1,001 reviews)
Excellent place to stay ! Comfortable beds and clean rooms . And a tasty breakfast ! Highly recommend .

Reviewed on May 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windham
View all trips

Windham Hotel Deals

Comfort Inn & Suites Cuyahoga Falls - Akron

Comfort Inn & Suites Cuyahoga Falls - Akron

3 out of 5
1420 Main St Cuyahoga Falls OH
Fully refundable
$98 nightly
The price is $113 total per night from May 31 to Jun 1
$113 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
Nice clean place

Reviewed on May 7, 2026

Comfort Inn & Suites Cuyahoga Falls - Akron
The Grand Resort

The Grand Resort

4 out of 5
9519 East Market Street Warren OH
9.4/10 Exceptional! (783 reviews)
Service horrible

Reviewed on Apr 14, 2026

Get rates
The Grand Resort
The Aurora Inn

The Aurora Inn

3 out of 5
30 Shawnee Trail Aurora OH
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $100 total per night from May 10 to May 11
$100 total
May 10 - May 11
Total with taxes and fees
9/10 Wonderful! (645 reviews)
Had a great weekend staying here. Between the kind staff that were all lovely to talk to, the beautiful indoor pool, and spacious room it was a good time the whole time. We definitely plan to stay next year when we come for our event again.

Reviewed on May 4, 2026

The Aurora Inn
See all 322 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Akron-Canton Airport (CAK)
Population
2,200
Top Sights
Nelson-Kennedy Ledges State Park, Robins Theatre and West Branch State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from $438 on Expedia for your Windham escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
November, December and January are the best times to search for cheap Windham vacation packages. Traveling in quieter periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Windham?
Typically, a handful of days is enough to visit the major attractions during your Windham vacation. But if you prefer to have more time to relax or take day trips, consider extending your itinerary.
How to find the best Windham package deals?
Begin your search for a Windham package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Windham package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windham escape off to a flying start.
Is it cheaper to book a Windham vacation as a package?
You can enjoy significant savings on your next Windham getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windham?
If you're planning a spur-of-the-moment Windham getaway, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Windham vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.