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Search results; Over 1,000 homes in Long Island

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Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 private bathroom
1–6 Oct
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4.82 out of 5 average rating, 51 reviews
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Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Long Island
500Island
4 bedrooms, 5 beds
2–9 Oct
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Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds
26–31 Oct
5.0 out of 5 average rating, 88 reviews
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Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 77 reviews
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Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds
11–16 Oct
4.95 out of 5 average rating, 43 reviews
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Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds
1–6 Oct
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Top guest favourite
Home in Portland
The Island House
3 bedrooms, 5 beds
1–6 Oct
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Flat in Peaks Island
Beach Front, Waterfront, Ferry Beach
2 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 51 reviews
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Top guest favourite
Room in Portland
Baxter’s Place: Private room; sleeps 2
1 queen bed
11–16 Oct
4.94 out of 5 average rating, 36 reviews
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Guest favourite
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms, 2 double beds
7–12 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Cabin in Portland
Sequester on Peaks Island
1 bedroom, 2 beds
1–6 May
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Rooms in Portland
Carrabassett Lodge
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 141 reviews
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Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed
6–11 Jun
4.94 out of 5 average rating, 17 reviews
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Guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
4 bedrooms, 4 beds
13–18 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Room in Peaks Island
Island Room with a View
1 double bed
19–24 Oct
4.97 out of 5 average rating, 115 reviews
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Guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds
25–30 Oct
4.97 out of 5 average rating, 67 reviews
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Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed
4–9 Oct
4.99 out of 5 average rating, 206 reviews