Search results; Over 1,000 homes in Windham

Guest favourite
Cottage in Windham
Peaceful waterfront hideaway with 5 bedrooms!
5 bedrooms, 7 beds, 1 private bathroom
26 Nov – 1 Dec
,
4.82 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
4.99 out of 5 average rating, 289 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Sept
Home in Windham
Lakeside escape in a family-friendly neighborhood.
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Sept
Top guest favourite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Home in Windham
Peaceful Garden Retreat
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 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
20–25 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 Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 192 reviews, 2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
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
8–13 Sept
Guest favourite
Cottage in Windham
Cozy Maine Lakefront Paradise
4.93 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 1 bathroom
9–14 Sept
Top guest favourite
Home in Gray
Coveside on Little Sebago
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
Top guest favourite
Home in Windham
Stunning, pets ok, private lake-house with dock.
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 1 bathroom
15–22 Aug
Top guest favourite
Flat in Windham
The Nest
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
4.95 out of 5 average rating, 44 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Windham
Pool, Hot tub & Lakes! Mins to Sebago
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
Flat in Cumberland
Cozy 1BR Near Portland, Freeport & Maine’s Coast
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug