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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!
4.95 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
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
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.96 out of 5 average rating, 235 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
New place to stay, 1 bedroom, 1 bed, 1 bathroom
2–7 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
24–29 Aug
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
26–31 Aug
Guest favourite
Flat in Westbrook
Cozy King bed apt near Portland with free parking
4.91 out of 5 average rating, 149 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
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, 148 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 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
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
5.0 out of 5 average rating, 60 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
Flat in Windham
Christmas Tree Farm apartment
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Guest favourite
Room in North Yarmouth
Conveniently located, quiet, in a wooded setting
4.81 out of 5 average rating, 115 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Gorham
The Maine Escape
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept