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Search results; Over 1,000 homes in Long Island

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Superhost
Cottage in Long Island
Grace Cottage
2 bedrooms, 5 beds, 2 private bathrooms
6–11 Oct
,
4.92 out of 5 average rating, 50 reviews
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Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 bathroom
1–6 Oct
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, 2.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
2–9 Oct
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Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 88 reviews
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Guest favourite
Cabin in Portland
Sequester on Peaks Island
1 bedroom, 2 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms, 2 double beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
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Top guest favourite
Rooms in Portland
Carrabassett Lodge
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 141 reviews
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Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms, 4 beds, 2 bathrooms
6–11 Dec
4.97 out of 5 average rating, 306 reviews
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Flat in Portland
Cozy studio apartment high up in the woods.
2 bedrooms, 2 beds, No bathroom
1–6 Jan
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Top guest favourite
Flat in Peaks Island
Beach Front, Waterfront, Ferry Beach
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 51 reviews
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Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
6–11 Jun
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
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, 2 bathrooms
11–16 Oct
4.95 out of 5 average rating, 43 reviews
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Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
3 bedrooms, 5 beds, 1 bathroom
4–11 Oct
4.83 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 reviews