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Search results; Over 1,000 homes in Windham

Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed
1–6 Sept
4.99 out of 5 average rating, 289 reviews
Home in Windham
Lakeside escape in a family-friendly neighborhood.
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds
22–27 Jul
4.97 out of 5 average rating, 231 reviews
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
10–15 Jul
New place to stay
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, 60 reviews
Guest favourite
Cabin in Gray
Chickadee Cottage
2 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 192 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 16 reviews
Flat in Cumberland
Cozy 1BR Near Portland, Freeport & Maine’s Coast
1 bedroom, 1 king bed
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Gorham
Beautiful Home In Gorham Maine
1 bedroom, 1 king bed
1–6 Sept
4.99 out of 5 average rating, 169 reviews
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms, 2 king beds
12–17 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Yurt in Windham
Sebago Sunrise Yurt - Trail Access!
1 bedroom, 1 queen bed
13–18 Jul
4.98 out of 5 average rating, 118 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds
4–9 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Standish
Arthur's Place • Sebago Lakefront • Near Windham
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds
25–30 Aug
4.9 out of 5 average rating, 96 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, 52 reviews
Top guest favourite
Home in Gray
The Lazy Hummingbird - Little Sebago Home w/ Sauna
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 36 reviews
Guest favourite
Guest suite in Raymond
Sebago Lake Waterfront Studio
2 beds
13–18 Sept
4.96 out of 5 average rating, 95 reviews