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Search results; Over 1,000 homes in Windham

Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.84 out of 5 average rating, 164 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
3–8 Oct
4.99 out of 5 average rating, 292 reviews
Guest favourite
Home in Windham
Lakeside escape in a family-friendly neighborhood.
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
22–27 Jul
4.97 out of 5 average rating, 232 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
14–19 Jul
New place to stay
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, 193 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
25–30 Jul
4.97 out of 5 average rating, 60 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
18–23 Jul
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
8–13 Aug
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds, 1 bathroom
25–30 Aug
4.9 out of 5 average rating, 96 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.96 out of 5 average rating, 51 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, 16 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 Gorham
Pond View Cottage
2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Gorham
Beautiful Home In Gorham, ME. (& no booking fees!)
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 169 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, 37 reviews