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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, 299 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds
4–9 Oct
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds
12–17 Sept
5.0 out of 5 average rating, 64 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds
21–26 Sept
4.92 out of 5 average rating, 51 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds
17–22 Oct
4.95 out of 5 average rating, 198 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds
29 Aug – 3 Sept
New place to stay
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds
20–25 Sept
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Windham
The Purple House by Pettingill Pond
3 bedrooms, 4 beds
25–30 Sept
4.9 out of 5 average rating, 99 reviews
Top guest favourite
Flat in Gray
Two bedroom duplex across st from crystal lake
2 bedrooms, 3 beds
15–20 Sept
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Windham
The Nest
1 bedroom, 2 beds
23–28 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 56 reviews
Guest favourite
Tiny home in Casco
Casco Tiny house, and HOT TUB!
1 bedroom, 2 beds
16–21 Aug
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds
6–11 Oct
4.96 out of 5 average rating, 72 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
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed
7–12 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guest house in Raymond
Raymond Sebago Cabin | Private EV+ Fire Pit
2 bedrooms, 2 beds
17–22 Aug
4.91 out of 5 average rating, 149 reviews