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Search results; Over 1,000 homes in Windham

Top guest favourite
Holiday home in Windham
Sebago Lakehouse: Hot Tub and Private Beach Access
3 bedrooms, 4 beds, 2 private bathrooms
27 Aug – 2 Sept
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4.99 out of 5 average rating, 103 reviews
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
4.99 out of 5 average rating, 294 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Oct
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
4.95 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.97 out of 5 average rating, 234 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
4.93 out of 5 average rating, 214 reviews, 2 beds, 1 bathroom
17–22 Sept
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
Guest favourite
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
4.78 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Room in Cumberland
Solar Powered Cape close to Portland/Maine Coast.
5.0 out of 5 average rating, 5 reviews, 1 queen bed, 1 bathroom
5–10 Aug
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 6 beds, 1.5 bathrooms
30 Aug – 4 Sept
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
New place to stay, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–19 Oct
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Oct
Guest favourite
Guest house in Raymond
Raymond Sebago Cabin | Private EV+ Fire Pit
4.91 out of 5 average rating, 147 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Aug
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Windham
Cozy Camp on the lake
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
Guest favourite
Cottage in Windham
Windham , Me Cottage with a view
4.91 out of 5 average rating, 35 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
5.0 out of 5 average rating, 59 reviews, 4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
4.97 out of 5 average rating, 61 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Sept
Top guest favourite
Cabin in Gray
Chickadee Cottage
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Jun