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Search results; Over 1,000 homes in Windham

Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 beds, 1 private bathroom
17–22 Oct
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4.96 out of 5 average rating, 200 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds
7–12 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed
18–23 Oct
4.99 out of 5 average rating, 300 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds
26 Sept – 1 Oct
4.92 out of 5 average rating, 52 reviews
Guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds
15–20 Oct
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds
25–30 Sept
4.9 out of 5 average rating, 100 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds
1–6 Sept
New place to stay
Home in Windham
Quiet Garden Home near lakes & downtown Windham
1 bedroom, 2 beds
27 Sept – 2 Oct
New place to stay
Home in Windham
Waterfront home on Pettingill Pond, Windham, ME
3 bedrooms, 4 beds
4–9 Sept
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms, 3 beds
5–10 Oct
4.94 out of 5 average rating, 64 reviews
Top guest favourite
Cabin in Windham
Private Hilltop Cabin, Lakes and Trails Abound..
3 bedrooms, 6 beds
14–19 Sept
4.92 out of 5 average rating, 214 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds
15–20 May
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed
7–12 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds
14–19 Nov
5.0 out of 5 average rating, 150 reviews