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
The price is $122 total per night from Nov 2 to Nov 3
$122 total
per night
Nov 2 - Nov 3
Stay at this 3-star 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! (1,009 reviews)
"Would stay again"

Reviewed on Oct 19, 2025

Dormir
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
The price is $92 total per night from Nov 11 to Nov 12
$92 total
per night
Nov 11 - Nov 12
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 ...
7.8/10 Good! (1,168 reviews)
"The free shuttle was right on time. We stayed here to catch a super early bus to NYC. We have stayed here before. The staff is friendly. The room is very comfortable and it's a great place to stay when you're catching a bus."

Reviewed on Oct 20, 2025

Clarion Hotel Portland
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
The price is $165 total per night from Nov 16 to Nov 17
$165 total
per night
Nov 16 - Nov 17
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
9.2/10 Wonderful! (1,632 reviews)
"It was a very nice and comfortable hotel. Walkable to everything. I would stay here agaiin."

Reviewed on Oct 19, 2025

Portland Harbor Hotel
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
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point ...
9.8/10 Exceptional! (84 reviews)
"Loved this place and would definitely stay here next time we go back."

Reviewed on Oct 15, 2025

The Weldon Hotel
68 East Grand Ave

68 East Grand Ave

3 out of 5
68 E Grand Ave, Old Orchard Beach, ME
Stay at this 3-star apartment in Old Orchard Beach. Enjoy free WiFi, free parking, and air conditioning. Popular attractions Old Orchard Beach Pier and Old Orchard ...
8.4/10 Very Good! (9 reviews)
"Nicole deserves a raise! She was helpful and informative with any of our inquiries. The unit could use a few more pans etc. for reheating the delicious Maine fried seafood! Bathroom could use a new shower curtain and grout! Would definitely stay here again!!"

Reviewed on Aug 26, 2025

68 East Grand Ave
Bright and airy condo with beachfront access and walkable entertainment nearby

Bright and airy condo with beachfront access and walkable entertainment nearby

Old Orchard Beach
Book a stay at this beach apartment in Old Orchard Beach. Enjoy a beach locale, a water park, and cable/satellite TV service. Popular attractions Old Orchard ...
7.4/10 Good! (3 reviews)
"Ease of beach access."

Reviewed on Sep 14, 2025

Bright and airy condo with beachfront access and walkable entertainment nearby
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

Things to do

Reviews of Windham

4.4
Top Destination
5 - Excellent
26
5 - Excellent 47%
4 - Good
24
4 - Good 44%
3 - Okay
4
3 - Okay 7%
2 - Disappointing
1
2 - Disappointing 2%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Loved area. Also reasonable distance from Portland as well as the White Mountains. Very enjoyable trip with family.

2/5 - Disappointing

Verified traveler

They need to widen the roads, so much traffic.

4/5 - Good

Jen

A good place to stay. Just bring socks and a white noise machine.

4/5 - Good

Verified traveler

It was a very busy road tk tuen left out of the property. Maybe lights in the future?

3/5 - Okay

Verified traveler

Highly recommend Kelly’s for breakfast and Mosquitos for ice cream.

4/5 - Good

Verified traveler

I was only there for 1 night

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