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Search results; Over 1,000 homes in Windham

Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
Studio, 2 beds, 1 private bathroom
17–22 Sept
,
4.93 out of 5 average rating, 214 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
26–31 Aug
New place to stay
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds
12–17 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed
3–8 Oct
4.99 out of 5 average rating, 294 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 53 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds
9–14 Sept
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds
17–22 Oct
4.95 out of 5 average rating, 195 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, 97 reviews
Superhost
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
2 bedrooms, 3 beds
1–6 Aug
4.78 out of 5 average rating, 32 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds
16–21 Aug
4.96 out of 5 average rating, 235 reviews
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds
14–19 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Cabin in Windham
Updated Cabin Little Sebago Lake
4 bedrooms, 5 beds
8–13 Jul
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds
9–14 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds
20–25 Sept
4.97 out of 5 average rating, 61 reviews
Guest favourite
Cottage in Windham
Beautiful Sebago Lakes Region
2 bedrooms, 3 beds
22–29 Aug
4.83 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds
1–6 Aug
5.0 out of 5 average rating, 21 reviews