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Search results; Over 1,000 homes in Windham

Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 private bathroom
14–19 Oct
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4.96 out of 5 average rating, 240 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
1–6 Dec
4.99 out of 5 average rating, 303 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 203 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Home in Gray
The Lazy Hummingbird - Little Sebago Home w/ Sauna
3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Oct
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Gorham
Luxe Architectural Gem near Portland/Lakes
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 222 reviews
Top guest favourite
Home in Raymond
Lakeside Cabin
2 bedrooms, 3 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Standish
Arthur's Place • Sebago Lakefront • Near Windham
2 bedrooms, 3 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Raymond
Sebago Lake Waterfront Studio
2 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Oct
4.97 out of 5 average rating, 32 reviews
Home in Frye Island
Peaceful Frye Island Stay – Cozy Family Comfort
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Falmouth
Family Lakehouse with Private Beach near Portland
3 bedrooms, 7 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 7 reviews