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Search results; Over 1,000 homes in Windham

Top guest favourite
Holiday home in Windham
Sebago Lakehouse: Hot Tub and Private Beach Access
3 bedrooms, 4 beds, 2 private bathrooms
9–15 Jul
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4.99 out of 5 average rating, 100 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.99 out of 5 average rating, 289 reviews
Home in Windham
Lakeside escape in a family-friendly neighborhood.
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.98 out of 5 average rating, 84 reviews
Guest favourite
Home in Windham
Peaceful Garden Retreat
1 bedroom, 2 beds, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 192 reviews
Guest favourite
Cottage in Windham
Cozy Maine Lakefront Paradise
3 bedrooms, 5 beds, 1 bathroom
9–14 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.9 out of 5 average rating, 96 reviews
Top guest favourite
Home in Gray
Coveside on Little Sebago
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Windham
Stunning, pets ok, private lake-house with dock.
3 bedrooms, 5 beds, 1 bathroom
15–22 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Windham
Pool, Hot tub & Lakes! Mins to Sebago
4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 25 reviews
Guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 20 reviews
Flat in Cumberland
Cozy 1BR Near Portland, Freeport & Maine’s Coast
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 4 reviews