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Search results; Over 1,000 homes in Long Island

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Guest favourite
Home in Long Island
Whole house on a great island in Casco Bay!
3 bedrooms, 4 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.99 out of 5 average rating, 76 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
19–25 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
17–22 Sept
5.0 out of 5 average rating, 3 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
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
19–24 Sept
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Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 17 reviews
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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, 204 reviews
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Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 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, 76 reviews
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Superhost
Home in Yarmouth
Beautiful home on Broad Cove
4 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
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Guest favourite
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
18–23 Sept
4.89 out of 5 average rating, 18 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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Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
3 bedrooms, 5 beds, 1 bathroom
20–27 Sept
4.83 out of 5 average rating, 18 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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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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Flat in Portland
Cozy studio apartment high up in the woods.
2 bedrooms, 2 beds, No bathroom
20–25 Sept