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Search results; Over 1,000 homes

Top guest favourite
Home in Cumberland
Water views, privacy, decks, minutes to Portland
4 bedrooms, 4 beds, 3.5 private bathrooms
31 Jan – 5 Feb
,
4.99 out of 5 average rating, 105 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
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 88 reviews
Superhost
Home in Windham
Lakeside Retreat | Lake Access | Grill & Fire Pit
4 bedrooms, 9 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Oxford
Exclusive Waterfront Cabin | Sauna | Private Beach
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 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, 22 reviews
Top guest favourite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 203 reviews
Top guest favourite
Home in Portland
Home in Portland
4 bedrooms, 9 beds, 1.5 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Raymond
Beautiful Lakefront View, on Sebago Lake
3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Naples
Trickey Moose Family Retreat | Fire Pit Kayaks
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 74 reviews
Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
3 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Standish
Dockside Dreams
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Gray
La Casita: Little Sebago Lake with hot tub!
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 5 reviews
Cottage in Raymond
Crescent Oak Cottage | Maine Lake Escape
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 4 Oct
New place to stay
Top guest favourite
Guest suite in Freeport
Studio Apartment in Freeport
3 beds, 1 bathroom
24–29 Sept
4.97 out of 5 average rating, 144 reviews
Guest favourite
Home in Raymond
Easy Living on Little Sebago
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 24 reviews