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Search results; Over 1,000 homes in Long Island

Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 private bathroom
27 Sept – 4 Oct
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4.82 out of 5 average rating, 49 reviews
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
5.0 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
26 Sept – 1 Oct
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
Guest favourite
Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
4.83 out of 5 average rating, 18 reviews, 3 bedrooms, 5 beds, 1 bathroom
23–30 Aug
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
4.7 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 1 bathroom
1–8 Aug
Guest favourite
Cottage in Portland
Peaks Island Waterfront
4.93 out of 5 average rating, 117 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
5.0 out of 5 average rating, 68 reviews, 3 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
Guest favourite
Flat in Portland
Peaks Island Casco Bay View Condo w/ Beach Access
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
Top guest favourite
Home in Scarborough
Captain Vacation House by beach, shopping, pets
5.0 out of 5 average rating, 47 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Aug
Top guest favourite
Home in Portland
Ocean Paradise Sunrise/Sunset Peaks Portland
5.0 out of 5 average rating, 81 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
26 Jul – 2 Aug
Top guest favourite
Flat in Portland
tHE nEST AT gRAY St. # 2
5.0 out of 5 average rating, 40 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Nov
Top guest favourite
Room in Peaks Island
Island Room with a View
4.97 out of 5 average rating, 108 reviews, 1 double bed, 1 bathroom
4–9 Jul
Top guest favourite
Flat in Peaks Island
Beach Front, Waterfront, Ferry Beach
5.0 out of 5 average rating, 44 reviews, 2 bedrooms, 3 beds, 1 bathroom
29 Aug – 5 Sept
Top guest favourite
Cottage in Harpswell
Private Waterfront, Fully Refreshed 1890s Cottage
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 7 beds, 2 bathrooms
5–10 Jul
Guest favourite
Cabin in Portland
Sequester on Peaks Island
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept