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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
18–23 Sept
,
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
27 Sept – 4 Oct
4.82 out of 5 average rating, 51 reviews
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Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
22–29 Sept
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Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
20–26 Sept
5.0 out of 5 average rating, 5 reviews
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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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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 Portland
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 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
20–25 Sept
5.0 out of 5 average rating, 77 reviews
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Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
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Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
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Superhost
Home in Portland
Classic Charm, Ocean View
5 bedrooms, 7 beds, 2 bathrooms
28 Sept – 3 Oct
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Guest favourite
Cabin in Portland
Sequester on Peaks Island
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 7 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, 12 reviews
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Cottage in Portland
Dream Maine Cottage on Peaks Island
3 bedrooms, 8 beds, 1.5 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 5 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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Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.7 out of 5 average rating, 20 reviews
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Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
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Guest favourite
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Oct
4.89 out of 5 average rating, 18 reviews