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Search results; Over 1,000 homes in Windham

Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
12–17 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, 59 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, 6 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds
21–26 Aug
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds
25–30 Aug
4.9 out of 5 average rating, 96 reviews
Superhost
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
2 bedrooms, 6 beds
30 Aug – 4 Sept
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, 194 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
4.97 out of 5 average rating, 234 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
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms, 3 beds
5–10 Oct
4.94 out of 5 average rating, 62 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, 28 reviews
Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 bedrooms, 2 queen beds
25–30 Aug
4.84 out of 5 average rating, 166 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds
14–19 Oct
5.0 out of 5 average rating, 17 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, 13 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
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds
17–22 Sept
4.93 out of 5 average rating, 213 reviews