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Search results; Over 1,000 homes in Long Island

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Guest favourite
Home in Long Island
Magical Long Island Retreat | Steps to Quiet Beach
7 bedrooms, 8 beds, 5.5 private bathrooms
1–6 Oct
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4.93 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Long Island
Ocean Side Cottage, Steps from the Beach
3 bedrooms, 5 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 15 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
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, 2.5 bathrooms
2–9 Oct
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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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Guest favourite
Home in Portland
BELLA VISTA - DIRECT OCEANFRONT at Elm Cove
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 27 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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Top guest favourite
Home in Portland
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 16 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, 86 reviews
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Home in Harpswell
Stover's Cove Beach Coastal Retreat
6 bedrooms, 8 beds, 3 bathrooms
2–7 Nov
4.69 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, WC
11–16 Oct
4.94 out of 5 average rating, 36 reviews
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Guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 67 reviews
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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
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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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Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
4 bedrooms, 4 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 13 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