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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, 99 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 288 reviews
Home in Windham
Lakeside escape in a family-friendly neighborhood.
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
New place to stay
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
Flat in Windham
Maple Brook
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 15 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
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 28 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
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Home in Gray
The Lazy Hummingbird - Little Sebago Home w/ Sauna
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 35 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 Gorham
Pond View Cottage
2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Standish
Sebago Lake Cottage | Rare Private Beach & Views
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 81 reviews
Guest favourite
Home in Windham
Peaceful Garden Retreat
1 bedroom, 2 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 131 reviews
Top guest favourite
Guest house in Gorham
Cozy 2BR retreat min toUSM&Sebago
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Gorham
Cute and cozy ranch
4 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Gray
Remodeled Lakefront on Little Sebago w dock+kayaks
4 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 24 reviews
Home in Yarmouth
Sugar Cube: Sweetest home in coastal Maine
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 5 reviews