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.

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$254 nightly
The price is $281 total per night from May 31 to Jun 1
$281 total
May 31 - Jun 1
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! (1,769 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."

Reviewed on May 25, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
$182 nightly
The price is $202 total per night from May 31 to Jun 1
$202 total
May 31 - Jun 1
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! (1,657 reviews)
"The place is wonderful. Just remember to get water from the lobby because it is not stocked in the rooms."

Reviewed on May 27, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$196 nightly
The price is $217 total per night from May 31 to Jun 1
$217 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.4/10 Exceptional! (1,223 reviews)
"We stay here every time we visit our daughter in Portland."

Reviewed on May 27, 2026

Cambria Hotel Portland Downtown-Old Port
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 Golf Learning Center and Riverside Municipal Golf ...
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.

Popular places to visit

Cities near Windham

Explore a world of travel with Expedia