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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
3–8 Oct
,
4.99 out of 5 average rating, 291 reviews
Guest favourite
Home in Windham
Lakeside escape in a family-friendly neighborhood.
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 193 reviews, 2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.97 out of 5 average rating, 232 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
4.97 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
13–19 Jul
Guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
4.96 out of 5 average rating, 50 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
4.9 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 1 bathroom
25–30 Aug
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
Top guest favourite
Home in Gorham
Pond View Cottage
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct
Top guest favourite
Home in Gray
Beautiful lakefront home on Little Sebago Lake
4.98 out of 5 average rating, 60 reviews, 4 bedrooms, 8 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Yurt in Windham
Sebago Sunrise Yurt - Trail Access!
4.98 out of 5 average rating, 122 reviews, 1 bedroom, 1 bed, Toilet with sink
27 Jul – 1 Aug
Top guest favourite
Home in Gray
The Lazy Hummingbird - Little Sebago Home w/ Sauna
5.0 out of 5 average rating, 37 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Sept
Top guest favourite
Home in Windham
Cozy Camp on the lake
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
Top guest favourite
Home in Gorham
Beautiful Home In Gorham, ME. (& no booking fees!)
4.99 out of 5 average rating, 169 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Cottage in Raymond
Quiet lakefront cottage with awesome wildlife
2 bedrooms, 3 beds, 2 bathrooms
26 Jul – 2 Aug
Top guest favourite
Home in Raymond
Spacious Lakehouse +Private Dock+Firepit+Kayaks
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 2 beds, 2 bathrooms
5–10 Oct