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Search results; Over 1,000 homes in Windham

Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 beds, 1 private bathroom
17–22 Oct
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4.96 out of 5 average rating, 200 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, 13 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
24–29 Sept
4.96 out of 5 average rating, 237 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.92 out of 5 average rating, 52 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.97 out of 5 average rating, 62 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds, 2.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 300 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, 100 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 188 reviews
Home in Windham
Quiet Garden Home near lakes & downtown Windham
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
New place to stay
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds, 2 bathrooms
6–11 Oct
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
3–8 Nov
4.93 out of 5 average rating, 219 reviews
Room in Frye Island
Waterfront Island Yoga #3
1 bed, 1 bathroom
4–9 Sept
New place to stay
Top 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, 14 reviews