Windham Vacations from $452

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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.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $537, price is now $452 per person
$452
per person
Jan 19 - Jan 23
found 17 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
Staff was great and room was exactly what we needed with lots of space!

Reviewed on Oct 19, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,149, price is now $898 per person
$898
per person
Jan 16 - Jan 23
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Our Bed and Breakfast was amazing! The bed was comfortable and we loved the salted chocolate chip cookies at night! The staff was so kind and hospitable!

Reviewed on Nov 2, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $634, price is now $501 per person
$501
per person
Jan 16 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Clean room, staff was very helpful and nice!!

Reviewed on Nov 5, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $725, price is now $605 per person
$605
per person
Jan 16 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

84 Main

84 Main

4 out of 5
Price was $754, price is now $634 per person
$634
per person
Dec 19 - Dec 22
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (51 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!

Reviewed on Oct 26, 2025

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Discover the most popular places to visit in Windham

Seacoast Adventure

5/5(4 reviews)

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, Maine: Tour in Vintage Fire Engine

Portland, Maine: Tour in Vintage Fire Engine

$43
per adult
90% of travellers recommend
Portland, Maine: Tour in Vintage Fire Engine
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

$49
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
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
$93 nightly
The price is $101 total per night from Nov 9 to Nov 10
$101 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,015 reviews)
Great hotel, I am glad I picked them. The room was comfortable and updated. Rooms do include a refrigerator and microwave.

Reviewed on Nov 5, 2025

Dormir
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 30 to Dec 1
$183 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,685 reviews)
Great service

Reviewed on Nov 6, 2025

Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 11 to Nov 12
$92 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (1,218 reviews)
It was clean and quiet-what I needed!

Reviewed on Nov 3, 2025

Clarion Hotel Portland
See all 3,110 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
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
State Theatre, East End Beach and Portland Museum of Art

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Frequently asked questions

How much does a Windham vacation package cost?
Offering great value package deals from $452 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.