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Search results; Over 1,000 homes in Windham

Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
5.0 out of 5 average rating, 59 reviews, 4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
4.99 out of 5 average rating, 294 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Oct
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
21–26 Aug
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
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
Superhost
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
2 bedrooms, 6 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Guest favourite
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
4.78 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.97 out of 5 average rating, 234 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
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
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
4.94 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
5.0 out of 5 average rating, 28 reviews, 4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–19 Oct
Guest favourite
Cottage in Windham
Cozy camp near highland lake
4.84 out of 5 average rating, 166 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Aug
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
9–14 Oct
Guest favourite
Cottage in Windham
Beautiful Sebago Lakes Region
4.83 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
4.93 out of 5 average rating, 213 reviews, 2 beds, 1 bathroom
17–22 Sept