Windham, ME

Travel Guide

A lake surrounded by houses and trees with autumn foliage.
A white church with a steeple and red accents, surrounded by autumn trees.
A residential street with houses, autumn foliage, and parked cars.
A welcome sign to Windham, founded 1737, with a logo for Windham Eagles.
A road with directional signs for Route 202 East and Route 4 North, surrounded by autumn foliage.
With outdoor recreation opportunities and an array of historical buildings to explore, this southern Maine town is full of charm.

Not far from Portland, Windham is worth visiting on its own. Enjoy outdoor recreation in the town’s many parks and forests, as well as on nearby Sebago Lake. Explore well-preserved buildings throughout town, from the Old Town Library to the Town Hall.

Stroll or bike through the woodlands and wetlands of Donnabeth Lippman Park or canoe or kayak on 10-acre (4-hectare) Chaffin Pond. Hike the loop trail around the pond. In winter, snowshoe or cross-country ski. Bring young children to the fun Story Walk and playground. In warmer months, anglers can cast a line in the pond here.

Summer is an especially bustling time in Windham. Check out Summerfest in June, with a parade and car show, or appreciate the 19th-century crafts at the Artisans on the Green exhibition, put on by the Windham Historical Society. Park along the edge of Claman Sanctuary and pick wild blueberries in July or August. For unique wildlife watching, head to Lowell Preserve to explore the porcupine caves.

Get outside in Windham during winter. Enjoy groomed cross-country skiing and snowshoeing trails at Lowell Preserve. Snowshoes in adult and youth sizes are free to borrow and use.

Nearby, the Mountain Division Trail and Sebago to the Sea Trail offer a shared-use route from Sebago Lake to Casco Bay. Follow the southern portion for 6 miles (10 kilometers) of this statewide trail from Windham to Standish.

Delve into Windham’s past at historic buildings maintained by the Windham Historical Society at the Village Green. The Old Town Library operated from 1907 to 1972 and today welcomes visitors to see original furnishings and displays. At the Old Grocery, originally a tailor’s shop, view a wide range of Windham artifacts.

Find Windham in southern Maine, less than a 30-minute drive from Portland. Visit year round to experience this town’s many outdoor activities and its New England history.

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
$108 nightly
The price is $119 total per night from Nov 22 to Nov 23
$119 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,005 reviews)
"Good stay"

Reviewed on Nov 3, 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
$81 nightly
The price is $89 total per night from Nov 10 to Nov 11
$89 total
Nov 10 - Nov 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,843 reviews)
"The hotel is a little run down, and it needs to be updated. Overall clean. The noise was brutal, there were some laud guests."

Reviewed on Nov 3, 2026

Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
$62 nightly
The price is $68 total per night from Nov 11 to Nov 12
$68 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn & Suites South 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.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
54 York St Portland ME
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Cross Insurance Arena ...
The Weldon Hotel
Evalina Hotel

Evalina Hotel

2.5 out of 5
215 Commercial St Portland ME
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions State Theatre and Thompson's Point ...
10/10 Exceptional! (18 reviews)
"Fabulous rental! The location was great could walk to restaurants, shopping, sightseeing. Place was very clean, beds comfortable and stocked with everything you need. Thank you for a wonderful stay in Portland."

Reviewed on Nov 3, 2026

Evalina Hotel
Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!

Portland ME
Stay at this apartment in Portland. Enjoy an in-room coffeemaker and air conditioning. Popular attractions State Theatre and Cross Insurance Arena are located ...
8.2/10 Very Good! (25 reviews)
"Location was convenient to everything and building was super secure."

Reviewed on Oct 18, 2026

Studio Apartment near downtown Walkable!
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.

Stay near popular Windham attractions

Things to do

Frequently asked questions

Is Windham worth visiting?
Windham is worth visiting for its engaging attractions, including Seacoast Adventure and the relaxing beach near Boathouse Beach Lane. Travelers can also enjoy a variety of dining experiences, with local restaurants serving Italian and North American cuisine.
When is the best time to visit Windham?
The best time to visit Windham is from May through September. For travelers seeking fewer crowds and better value, the quieter months of December through March are a good option, with cooler temperatures and snowy conditions often present during this period.
What is Windham known for?
Windham is known for Seacoast Adventure, offering travelers outdoor fun. This city also features a relaxing beach near Boathouse Beach Lane. Travelers can also find Italian food, adding to the local culinary experience.
What is a good itinerary length for Windham?
A good itinerary length for Windham is two to three days to enjoy Seacoast Adventure and the beach near Boathouse Beach Lane. For an extended stay of four to five days, travelers can also experience activities like the Fall Covered Bridge Kayak Tour or the Fall Foliage Covered Bridge Tour by Kayak in Southern Maine. See Windham Activities.
What are the top things to do in and around Windham?
Windham offers outdoor adventures and scenic natural beauty for travelers to enjoy:

  • Explore Seacoast Adventure.
  • Relax at the beach near Boathouse Beach Lane.
  • Take a Fall Covered Bridge Kayak Tour in Southern Maine.

How do I plan a trip to Windham?
To plan your trip to Windham, book flights, hotels, and rental cars in advance. Consider activities like Seacoast Adventure and the beach near Boathouse Beach Lane. For outdoor fun, look into Fall Covered Bridge Kayak Tours, especially during autumn. Always pair outdoor plans with indoor backups for weather flexibility, ensuring a smooth trip.
What cuisines can you find in Windham?
In Windham you can find Mediterranean cuisine, with dishes like hummus, gyros, and falafel. Travelers can also enjoy Italian, North American, and Asian options, along with Latin American choices such as Mexican food. The area also offers coffee shops and speakeasy bars.
Can I book a refundable hotel in Windham?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Windham by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Windham with Expedia?
Expedia makes it easier to plan your Windham trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Windham?
The best choice depends on your travel style. Hotels in Windham can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Windham trip on Expedia?
Once you've booked your Windham trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Windham trip?
Expedia offers customer support before, during, and after your Windham trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Windham?
If it's your first trip to Windham, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Windham hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Windham hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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