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Search results; Over 1,000 homes in Windham

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Guest favourite
Cottage in Windham
Peaceful waterfront hideaway with 5 bedrooms!
5 bedrooms, 7 beds, 1 private bathroom
26 Nov – 1 Dec
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4.82 out of 5 average rating, 51 reviews
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Home in Windham
Beautiful Sebago Lake Getaway!
2 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 67 reviews
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Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 56 reviews
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Guest favourite
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
27 Oct – 1 Nov
4.95 out of 5 average rating, 204 reviews
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Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
13–18 Oct
4.93 out of 5 average rating, 224 reviews
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Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
14–19 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Cabin in Windham
Updated Cabin Little Sebago Lake
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds, 1 bathroom
15–20 May
4.98 out of 5 average rating, 62 reviews
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Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.9 out of 5 average rating, 102 reviews
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Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms, 3 beds, 2 bathrooms
19–24 Oct
4.94 out of 5 average rating, 69 reviews
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Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds, 2 bathrooms
6–11 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 65 reviews
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Guest favourite
Cottage in Windham
Windham , Me Cottage with a view
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
4.91 out of 5 average rating, 35 reviews
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Home in Windham
Waterfront home on Pettingill Pond, Windham, ME
3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Oct
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Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
4.96 out of 5 average rating, 240 reviews