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Search results; Over 1,000 homes in Windham

Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 beds, 1 private bathroom
17–22 Oct
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4.96 out of 5 average rating, 202 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Windham
Waterfront Home w/fenced yard 15 mins to Portland
5 bedrooms, 7 beds
4–9 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Windham
1 Bedroom with Beach Access
1 bedroom, 2 beds
18–23 Oct
4.97 out of 5 average rating, 68 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, 66 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, 182 reviews
Top guest favourite
Camper van/Motorhome in Windham
Tiny House Camper - Trail Access!
1 bedroom, 2 beds
22–27 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds
25–30 Oct
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 21 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, 220 reviews
Guest favourite
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cabin in Windham
Own 50' Lake Front cozy Camp
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Windham
Sebago Lake Beach Paradise
3 bedrooms, 8 beds
7–12 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Cumberland
Easy Access To Portland | King Bed + Kitchen
1 bedroom, 1 king bed
12–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Windham
Maple Brook
2 bedrooms, 3 beds
19–24 Oct
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Standish
Arthur's Place • Sebago Lakefront • Near Windham
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Gray
The Lazy Hummingbird - Little Sebago Home w/ Sauna
3 bedrooms, 4 beds
24–29 Sept
5.0 out of 5 average rating, 45 reviews