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Search results; Over 1,000 homes in Windham

Top guest favourite
Home in Windham
Lakefront | Dock + Fire Pit Near Sebago & Portland
3 bedrooms, 5 beds, 1 private bathroom
4–9 Oct
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4.97 out of 5 average rating, 39 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
1–6 Dec
4.99 out of 5 average rating, 303 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 203 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 222 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 240 reviews
Top guest favourite
Home in Gray
Beautiful lakefront home on Little Sebago Lake
4 bedrooms, 8 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 64 reviews
Home in Windham
Beautiful Sebago Lake Getaway!
2 bedrooms, 4 beds, 1.5 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Cabin in Windham
Cozy Private Lake Getaway (Seasonal)
1 bedroom, 1 queen bed, 1 bathroom
2–7 Dec
4.92 out of 5 average rating, 61 reviews
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Gorham
Luxe Architectural Gem near Portland/Lakes
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Guest suite in Raymond
Sebago Lake Waterfront Studio
2 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Home in Raymond
Lakeside Cabin
2 bedrooms, 3 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 6 reviews