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Search results; Over 1,000 homes in Windham

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, 213 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
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
9–14 Oct
Top guest favourite
Flat in Windham
Maple Brook
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–19 Oct
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
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
Guest favourite
Guest house in Raymond
Raymond Sebago Cabin | Private EV+ Fire Pit
4.91 out of 5 average rating, 146 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Aug
Top guest favourite
Room in South Portland
Peaceful Wooded Oasis Near Portland & Beaches
4.98 out of 5 average rating, 109 reviews, 1 queen bed, 1.5 bathrooms
2–7 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
Guest favourite
Home in Windham
Windham Lake Retreat | Knotty Pine Cabin Fire pit
4.94 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
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
Flat in Windham
Christmas Tree Farm apartment
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Guest suite in Raymond
Sebago Lake Waterfront Studio
4.96 out of 5 average rating, 98 reviews, 2 beds, 1 bathroom
1–6 Oct
Guest favourite
Cabin in Raymond
Sebago Lake Cottage on Raymond Cape
4.91 out of 5 average rating, 80 reviews, 1 bedroom, 4 beds, 1 bathroom
2–7 Sept