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Search results; Over 1,000 homes in Windham

Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 bedrooms, 2 beds, 1 private bathroom
26 Sept – 1 Oct
,
4.84 out of 5 average rating, 168 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
9–14 Sept
4.92 out of 5 average rating, 50 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.99 out of 5 average rating, 298 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 196 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds, 1 bathroom
25–30 Sept
4.9 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.96 out of 5 average rating, 236 reviews
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.94 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Windham
Updated Cabin Little Sebago Lake
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Cabin in Windham
Private Hilltop Cabin, Lakes and Trails Abound..
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 213 reviews