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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
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4.99 out of 5 average rating, 292 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
14–19 Jul
Guest favourite
Home in Windham
Lakeside escape in a family-friendly neighborhood.
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
4.92 out of 5 average rating, 49 reviews, 2 bedrooms, 5 beds, 2.5 bathrooms
8–13 Aug
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
18–23 Jul
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.97 out of 5 average rating, 232 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
4.9 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 1 bathroom
25–30 Aug
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
4.97 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Guest favourite
Cottage in Windham
Cozy Maine Lakefront Paradise
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 5 beds, 1 bathroom
9–14 Sept
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 193 reviews, 2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
Top guest favourite
Home in Windham
Cozy Camp on the lake
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
Guest favourite
Cottage in Windham
Cozy camp near highland lake
4.84 out of 5 average rating, 164 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
4.94 out of 5 average rating, 62 reviews, 3 bedrooms, 6 beds, 2 bathrooms
3–8 Oct
Top guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Sept