How much does a Windham vacation package cost?

Offering great value package deals from $417 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?

Pick your travel dates: What you want to do in Windham and your preferred season can help you decide when to get away. 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. 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. 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. 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. 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.

Book Windham Vacation Packages 2026

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.

84 Main

$417

per person

Mar 7 - Mar 11

found 20 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

10/10 Exceptional! (52 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

Portland Harbor Hotel

Downtown Portland

$615

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Reduce noise from patrons near elevator and coffee area on second floor, very loud

Reviewed on Jan 10, 2026

Cliff House Maine

Bald Head

Save 100% on your flight

$1,142

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

St. Louis (STL) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

Loved the hotel had a great time with a group of friends

Reviewed on Jan 12, 2026

The McKernan Inn

$676

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Portland (PWM)

9/10 Wonderful! (83 reviews)

Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

The Docent’s Collection – Thompson Block

Downtown Portland

$676

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Portland (PWM)

9.6/10 Exceptional! (249 reviews)

Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.

Reviewed on Jan 10, 2026

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Windham Hotel Deals

Dormir

965 Roosevelt Trail Windham ME

Fully refundableReserve now, pay when you stay

$109 nightly

$119 total

Jan 20 - Jan 21

Total with taxes and fees

8.8/10 Excellent! (1,010 reviews)

clean rooms, quiet, nice place

Reviewed on Jan 8, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$78 nightly

$87 total

Jan 18 - Jan 19

Total with taxes and fees

8/10 Very Good! (1,325 reviews)

Nice clean easy close to airport

Reviewed on Jan 14, 2026

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

$98 nightly

$108 total

Feb 1 - Feb 2

Total with taxes and fees

8.8/10 Excellent! (1,004 reviews)

Always great.

Reviewed on Jan 13, 2026

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.

Things to do in and around Windham

Windham, Maine, offers a perfect blend of outdoor adventures and scenic beauty, making it ideal for romantic getaways. Visitors can enjoy a variety of activities, including skiing at the local ski resort and exploring the picturesque landscapes. The area's charm and recreational options make it a great destination for those seeking both relaxation and adventure.

Shopping

The Maine Mall is a great spot for shopping, located 9 miles away from Windham, featuring entertainment and family-friendly vibes. If you're up for a drive, you can visit the LL Bean Flagship Store 16 miles away or explore The Willows Flea Market, 23 miles from Windham, for unique finds.

Recreation

Experience live music at Thompson's Point, a vibrant venue 9 miles from Windham that offers an electrifying atmosphere. For sports enthusiasts, Hadlock Field, also 9 miles away, hosts thrilling games. Enjoy a round of golf at Riverside Municipal Golf Course, just 5 miles from Windham, surrounded by beautiful scenery.

Adventure

Experience the thrill at Seacoast Adventure with exciting arcade games and family-friendly activities. Hike the scenic Rattlesnake Mountain Trail for breathtaking views, located 10 miles from Windham. For more fun, visit Bayside Bowl to enjoy arcade games and a lively atmosphere, also 10 miles away.

Nightlife

Windham offers a cozy nightlife with local favorites like The Frog & Turtle, where you can enjoy craft beers and live music. For a relaxed evening, visit the Windham Public Library's events, or unwind at a nearby bar with friends, soaking in the welcoming community vibe.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windham

Windham, Maine, is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore a variety of attractions, including historic colleges and universities, charming historic houses, and entertainment arenas. The area's points of interest cater to travelers looking for cultural experiences, outdoor activities, and beautiful beach settings, making it a delightful spot for a memorable vacation.

University of New England: A modern institution located 7 miles from Windham, the University of New England offers a vibrant campus atmosphere. Visitors can enjoy the blend of academic excellence and city vibes, making it a great spot for a leisurely stroll or to appreciate the architecture.
Portland Museum of Art: Situated 10 miles away, this museum showcases a rich collection of American and European art. With its cultural vibes, visitors can immerse themselves in art exhibitions and enjoy the beautiful architecture of the museum itself.
Cross Insurance Arena: Also located 10 miles from Windham, this entertainment venue is perfect for family-friendly events. Experience the excitement of live sports, concerts, and shows, all in a lively atmosphere that appeals to all ages.

Best time to go to Windham

The best time to visit Windham is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	24.6°F (-4.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	25.9°F (-3.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	32.9°F (0.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	43.7°F (6.5°C)	Light Rain	Mostly Cloudy	Slightly High	Average
May	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Average
June	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.7°F (20.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	62.2°F (16.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	51.6°F (10.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	31.6°F (-0.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Windham

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Windham.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

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