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Search results; Over 1,000 homes in Windham

Top guest favourite
Flat in Windham
The Roost - lovely one bedroom efficiency unit
1 bedroom, 1 bed, 1 private bathroom
6–11 Sept
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4.97 out of 5 average rating, 198 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 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, 50 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed
13–18 Oct
4.99 out of 5 average rating, 298 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds
2–7 Sept
4.96 out of 5 average rating, 236 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 10 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
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, 196 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds
4–9 Oct
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds
7–12 Aug
5.0 out of 5 average rating, 22 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, 63 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds
25–30 Sept
4.93 out of 5 average rating, 216 reviews
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds
19–24 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds
6–11 Oct
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms, 2 king beds
17–22 Oct
4.97 out of 5 average rating, 30 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, 55 reviews
Guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed
7–12 Sept
5.0 out of 5 average rating, 18 reviews