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Search results; Over 1,000 homes

Top guest favourite
Home in Cumberland
Rustic charm close to Portland
2 bedrooms, 3 beds, 2 shared bathrooms
2–7 Oct
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4.96 out of 5 average rating, 337 reviews
Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
18–23 Sept
4.97 out of 5 average rating, 174 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Raymond
Lovely Lakefront Cottage - Book Your Fall GetAway!
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Naples
Lakefront Estate | Hot Tub, Pool Table, Dock & Gym
6 bedrooms, 11 beds, 4 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 369 reviews
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Chalet in Standish
Blueberry Hill
5 bedrooms, 10 beds, 2.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 258 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Windham
Updated Cabin Little Sebago Lake
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 30 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Casco
Stunning 4,900 SF Lake House
4 bedrooms, 10 beds, 3.5 bathrooms
8–15 Sept
5.0 out of 5 average rating, 32 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds, 2.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 302 reviews
Top guest favourite
Home in Gray
La Casita: Little Sebago Lake with hot tub!
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Old Orchard Beach
OOB Oasis: 6BR Home w/ Private Pool Near Beach
6 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
4.95 out of 5 average rating, 154 reviews
Top guest favourite
Home in Windham
Private Pool and Hot Tub! Mins to Sebago Lake.
4 bedrooms, 5 beds, 2 bathrooms
15–20 Oct
4.97 out of 5 average rating, 32 reviews