Windham Vacations from $536

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Your Windham Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham vacation package. Book a hotel in Parkside, which is good for festivals, markets and walking. If your trip to Windham includes a little sightseeing, don't miss well-known attractions like Maine Wildlife Park, Riverside Municipal Golf Course and MAGAN Trailhead. Check out Expedia's wide range of travel options and begin planning your perfect vacation to Windham today.

The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection
The Weldon Hotel
Portland Harbor Hotel
Cliff House Maine
Inn By The Sea
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Discover the most popular places to visit in Windham

What to do in Windham

Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $252 total per night from Aug 20 to Aug 21
$252 total
Aug 20 - Aug 21
Total includes taxes and fees
8.8/10 Excellent! (999 reviews)
"Great for a quick stay, not for a long stay."

Reviewed on Aug 9, 2025

Dormir
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from Aug 20 to Aug 21
$127 total
Aug 20 - Aug 21
Total includes taxes and fees
7.8/10 Good! (1,180 reviews)
"Comfortable and quiet"

Reviewed on Aug 15, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total includes taxes and fees
7.8/10 Good! (1,016 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug 17, 2025

Clarion Hotel Portland
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?
Offering great value package deals from $536 on Expedia, you'll be surprised at how little a vacation to Windham costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Windham?
June, July and October are the best times to search for cheap Windham vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Windham?
Usually, a handful of days is enough to tick off the major sights during your Windham vacation. But if you want to have more time to relax or go on day trips, think about extending your trip.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Windham package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windham adventure underway.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Windham getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windham?
If you have your Windham travel dates finalized, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windham?

  1. Pick your travel dates: What you want to do in Windham and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Windham.
  3. Organize your Windham escape with Expedia's trip planning tool: Search for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Windham together.
  4. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Windham. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Windham vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our travel guide to find some incredible things to do in Windham. Book tickets or make reservations in advance to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're anything like us, you love traveling but don't love the 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 spread the cost of your Windham break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap 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.