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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
19–24 Sept
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4.92 out of 5 average rating, 50 reviews
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Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
22–29 Sept
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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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Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
21–27 Sept
5.0 out of 5 average rating, 5 reviews
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Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 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
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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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 Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
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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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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, 205 reviews
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Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
5.0 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
20–25 Sept
5.0 out of 5 average rating, 77 reviews
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Cottage in Portland
Dream Maine Cottage on Peaks Island
3 bedrooms, 8 beds, 1.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 5 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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Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Apr
5.0 out of 5 average rating, 39 reviews
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Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 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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Top guest favourite
Cottage in Portland
Captain's Quarters on Peaks Island
1 bedroom, 1 bed, 1 bathroom
1–6 Jan
4.98 out of 5 average rating, 40 reviews