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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
27 Aug – 2 Sept
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4.99 out of 5 average rating, 103 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.99 out of 5 average rating, 297 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 195 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
17–22 Sept
4.93 out of 5 average rating, 215 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.96 out of 5 average rating, 235 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
9–14 Sept
4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 55 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, 62 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds, 2 bathrooms
14–19 Oct
5.0 out of 5 average rating, 20 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.76 out of 5 average rating, 33 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, 54 reviews
Guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 bedrooms, 2 queen beds, 1 bathroom
26 Sept – 1 Oct
4.84 out of 5 average rating, 166 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds, 1 bathroom
7–12 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds, 1 bathroom
25–30 Sept
4.9 out of 5 average rating, 97 reviews
Guest favourite
Cottage in Windham
Windham , Me Cottage with a view
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.91 out of 5 average rating, 35 reviews