Search results; Over 1,000 homes in Windham

Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 bed, 1 shared bathroom
3–8 Oct
,
4.99 out of 5 average rating, 292 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
4 beds
14–19 Jul
New place to stay
Guest favourite
Home in Windham
Lakeside escape in a family-friendly neighborhood.
3 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
5 beds
8–13 Aug
4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
On the lake, Kayak
18–23 Jul
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
2 beds
22–27 Jul
4.97 out of 5 average rating, 232 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5 beds
11–16 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
4 beds
25–30 Aug
4.9 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
2 beds
25–30 Jul
4.97 out of 5 average rating, 60 reviews
Guest favourite
Cottage in Windham
Cozy Maine Lakefront Paradise
5 beds
9–14 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 queen beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 193 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Windham
Maple Brook
3 beds
15–20 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
5 beds
11–16 Oct
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
5 beds
5–10 Oct
5.0 out of 5 average rating, 52 reviews
Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 queen beds
30 Aug – 4 Sept
4.84 out of 5 average rating, 164 reviews
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
6 beds
3–8 Oct
4.94 out of 5 average rating, 62 reviews
Top guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
4 beds
3–8 Sept
4.98 out of 5 average rating, 84 reviews