Windham, ME

Travel Guide

Windham
Windham
Windham
Windham
Windham
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.

Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
$159 nightly
The price is $173 total per night from May 28 to May 29
$173 total
May 28 - May 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (999 reviews)
"Rooms were over priced, hot water for shower was limited, breakfast was average for this type of property."

Reviewed on May 19, 2026

Dormir
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$229 nightly
The price is $254 total per night from May 26 to May 27
$254 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
9.4/10 Exceptional! (1,764 reviews)
"Staff ensured our room on check in was quiet. Except there was a night club across the street. Then when asked for a new room was told by staff “that they would bet their career it would be quiet”. The room was one floor up on the same side … Couldn’t sleep until after 1am because of the club across ..."

Reviewed on May 22, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
$170 nightly
The price is $188 total per night from May 26 to May 27
$188 total
May 26 - May 27
Total with taxes and fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
9.4/10 Exceptional! (1,646 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."

Reviewed on May 20, 2026

Portland Regency Hotel & Spa
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.
WATERFRONT ON HIGHLAND LAKE.  LESS THAN 30 MINUTES TO PORTLAND

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

WINDHAM ME
Stay at this cottage in Windham. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Shaw Park and Riverside Municipal Golf Course are ...
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
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 Thompson's Point and ...
9.8/10 Exceptional! (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"

Reviewed on Apr 23, 2026

The Weldon Hotel
Lakefront Cottage: Boat Dock, Patio & Kayaks!

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3 out of 5
Oxford ME
Stay at this cottage in Oxford. Enjoy free parking, a garden, and patios. Popular attractions Oxford Plains Speedway and Oxford Casino are located nearby.
Lakefront Cottage: Boat Dock, Patio & Kayaks!
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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