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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
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4.99 out of 5 average rating, 295 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 195 reviews
Top guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
17–22 Sept
4.93 out of 5 average rating, 214 reviews
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
1 bedroom, 1 bed, 1 bathroom
2–7 Aug
New place to stay
Guest favourite
Cottage in Windham
Cozy house w/deeded beach access to Highland Lake
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.78 out of 5 average rating, 32 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
26–31 Aug
New place to stay
Guest favourite
Flat in Westbrook
Cozy King bed apt near Portland with free parking
1 bedroom, 1 king bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 149 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds, 2 bathrooms
14–19 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 60 reviews
Guest favourite
Guest house in Raymond
Raymond Sebago Cabin | Private EV+ Fire Pit
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Aug
4.91 out of 5 average rating, 148 reviews
Top guest favourite
Home in Windham
Cozy Camp on the lake
3 bedrooms, 5 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.96 out of 5 average rating, 235 reviews
Top guest favourite
Cabin in Gray
Chickadee Cottage
2 bedrooms, 4 beds, 1 bathroom
12–17 Jun
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Windham
Christmas Tree Farm apartment
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Windham
Enjoy Sunsets at Welcoming Lake Front Property
2 bedrooms, 5 beds, 2.5 bathrooms
9–14 Sept
4.92 out of 5 average rating, 49 reviews