Windham Vacations from $380

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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.
Dormir

Dormir

3 out of 5
Save 100% on your flight
Price was $518, price is now $380 per person
$380
per person
Oct 14 - Oct 17
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (1,003 reviews)
For the price I would have liked to have my bed made and fresh towels replaced every day. Breakfast was really good but ditch those fake eggs. Over all it was great. Would stay there again.

Reviewed on Aug 17, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,741, price is now $1,147 per person
$1,147
per person
Oct 3 - Oct 6
found 23 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $760, price is now $526 per person
$526
per person
Oct 27 - Oct 30
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.

Reviewed on Aug 22, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $987, price is now $744 per person
$744
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
nice building walkable to shopping + dining

Reviewed on Aug 22, 2025

Nonantum Resort

Nonantum Resort

3.5 out of 5
Save 100% on your flight
Price was $785, price is now $597 per person
$597
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (776 reviews)
Excellent property for families. I wouldn’t recommend it for couples.

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Windham

Maine Wildlife Park

Meet the animals who live at Maine Wildlife Park during your trip to Windham. While in this family-friendly area, you can savor the top-notch restaurants.

Maine Wildlife Park

Seacoast Adventure

Bring the family to Seacoast Adventure and enjoy some excitement at this amusement park in Windham. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

Seacoast Adventure

What to do in Windham

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$7
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

$67
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

$59
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities 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 25 to Aug 26
$252 total
Aug 25 - Aug 26
Total with taxes and fees
8.8/10 Excellent! (999 reviews)
"Breakfast Buffet"

Reviewed on Aug 18, 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
$107 nightly
The price is $117 total per night from Aug 26 to Aug 27
$117 total
Aug 26 - Aug 27
Total with taxes and fees
7.8/10 Good! (1,223 reviews)
Excellent choice for single night stay
"Very convenient hotel for those flying into PWM. Quick stop on the way to Rockland. Front desk was pleasant. Got me toothpaste I forgot. Told them about stopped up sink and they noted it. (It wasn't an issue for me as I simply removed the stopper and left it on the counter to be cleaned.) Breakfast ..."

Reviewed on Aug 22, 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 27 to Aug 28
$168 total
Aug 27 - Aug 28
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"I like the room and accommodations. The front desk person was a bit brief with me though."

Reviewed on Aug 22, 2025

Clarion Hotel Portland
See all 3,247 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?
Offering great value package deals from $380 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.