Windham Vacations from $263

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Aurora Inn

The Aurora Inn

3 out of 5
Price was $335, price is now $263 per person
$263
per person
Aug 13 - Aug 15
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Akron (CAK)
9/10 Wonderful! (684 reviews)
Pool was very nice. No elevator if on second floor and rooms did not mask sound well so late and early it was hard to sleep. Hotel was clean, central to town and very friendly staff!

Reviewed on Jun 23, 2026

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Save 100% on your flight
Price was $919, price is now $695 per person
$695
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cleveland (CLE)
9.6/10 Exceptional! (5 reviews)
InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $483, price is now $366 per person
$366
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
9/10 Wonderful! (906 reviews)
Front Desk Team Excelnt Bar and Returant Team did a great Job .

Reviewed on Jun 13, 2026

Hampton Inn Medina

Hampton Inn Medina

2.5 out of 5
Price was $664, price is now $523 per person
$523
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Akron (CAK)
8.8/10 Excellent! (1,023 reviews)
Very nice place to stay

Reviewed on Jun 27, 2026

Quality Lodge

Quality Lodge

2.5 out of 5
Price was $490, price is now $388 per person
$388
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Cleveland (CLE)
7.8/10 Good! (347 reviews)
Clean room close to Cedar Point would stay again

Reviewed on Oct 31, 2025

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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 Jul 19 to Jul 20
$113 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Be aware if you are coming back late, parking was bad. I found the last spot available in a corner behind the hotel in a poorly lit area. Thank goodness there was a car dealership next door that helped light up the parking lot. When we got there, a car was parked under the roof at the front door, ..."

Reviewed on Jun 28, 2026

Comfort Inn & Suites Cuyahoga Falls - Akron
The Aurora Inn

The Aurora Inn

3 out of 5
30 Shawnee Trail Aurora OH
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Jul 5 to Jul 6
$102 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (697 reviews)
"Great stay, although short. Would love to come back and enjoy the courtyard, restaurant and pool."

Reviewed on Jun 24, 2026

The Aurora Inn
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
$105 nightly
The price is $121 total per night from Jul 5 to Jul 6
$121 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (989 reviews)
"Our room was never cleaned as we were there for 3 nights. No whirl poor even though there was a sign in the lobby stating there is one. Food and drinks way too pricey. Bagel and cream cheese 8.50 however across the street only 2.50."

Reviewed on Jun 29, 2026

Courtyard by Marriott Akron Stow
See all 328 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

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Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from $263 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.