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Search results; Over 1,000 homes in Windham

Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds, 3 private bathrooms
12–17 Sept
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5.0 out of 5 average rating, 65 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed
18–23 Oct
4.99 out of 5 average rating, 302 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Windham
Sebago Lake Beach Paradise
3 bedrooms, 8 beds
4–10 Sept
4.96 out of 5 average rating, 28 reviews
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
2 bedrooms, 3 beds
1–6 Sept
4.76 out of 5 average rating, 34 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds
17–22 Oct
4.96 out of 5 average rating, 200 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds
7–12 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds
24–29 Sept
4.96 out of 5 average rating, 238 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds
3–8 Nov
4.93 out of 5 average rating, 219 reviews
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds
25–30 Oct
4.96 out of 5 average rating, 73 reviews
Superhost
Home in Windham
Waterfront Home w/fenced yard 15 mins to Portland
5 bedrooms, 7 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Home in Windham
Quiet Garden Home near lakes & downtown Windham
1 bedroom, 2 beds
26 Sept – 1 Oct
New place to stay
Home in Raymond
Lakeside Cabin
2 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds
2–7 Oct
4.97 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Cumberland
Private Suite Near Portland | King Bed + Kitchen
1 bedroom, 1 king bed
12–17 Oct
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds
1–6 Sept
New place to stay