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Search results; Over 1,000 homes in Windham

Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 bed, 1 shared bathroom
1–6 Nov
,
4.99 out of 5 average rating, 298 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 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
21–26 Sept
4.92 out of 5 average rating, 51 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds, 2.5 bathrooms
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 197 reviews
Superhost
Home in Falmouth
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 11 reviews
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, 65 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, 98 reviews
Guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
4.97 out of 5 average rating, 31 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, 56 reviews
Guest favourite
Cottage in Windham
Cozy camp near highland lake
2 bedrooms, 2 queen beds, 1 bathroom
26 Sept – 1 Oct
4.83 out of 5 average rating, 169 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 19 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, 17 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Cabin in Windham
Private Hilltop Cabin, Lakes and Trails Abound..
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 213 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 58 reviews
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.76 out of 5 average rating, 33 reviews