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Search results; Over 1,000 homes in Islesboro

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Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 beds, 1 private bathroom

10–15 Oct

$2,208 SGD for 5 nights

,

5.0 out of 5 average rating, 23 reviews

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Top guest favourite

Cottage in Islesboro

Islesboro Boathouse

1 bedroom, 1 bed, 1 bathroom

11–16 Oct

$3,168 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 116 reviews

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Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed, 1 bathroom

20–25 Oct

$1,038 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 69 reviews

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Guest favourite

Cottage in Islesboro

Ocean Front Island Cottage

2 bedrooms, 4 beds, 1 bathroom

13–18 Oct

$1,211 SGD for 5 nights

Free cancellation

4.82 out of 5 average rating, 60 reviews

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Guest favourite

Home in Islesboro

The Colony

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

Free cancellation

5.0 out of 5 average rating, 6 reviews

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Top guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds, 3.5 bathrooms

1–6 Oct

$3,968 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

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Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 6 beds, 1.5 bathrooms

5–12 Sept

$3,520 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 11 reviews

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Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds, 2.5 bathrooms

1–6 Oct

$2,151 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

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Guest favourite

Home in Islesboro

Blue Moon Cottage

3 bedrooms, 4 beds, 1.5 bathrooms

1–8 Oct

Weekly discount

4.83 out of 5 average rating, 23 reviews

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Home in Islesboro

Island Home

5 bedrooms, 6 beds, 2.5 bathrooms

3–10 Oct

$5,583 SGD for 7 nights

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Cabin in Islesboro

Maine Island Cabin, seaside gem

1 bedroom, 2 beds, 1 bathroom

31 Jul – 5 Aug

$1,507 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

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Guest favourite

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds, 2 bathrooms

1–6 Dec

$3,194 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 9 reviews

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Home in Islesboro

The Anchorage

4 bedrooms, 5 beds, 2 bathrooms

10–15 Oct

Free cancellation

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Top guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds, 1 bathroom

2–7 Oct

$4,306 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

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Top guest favourite

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds, 2 bathrooms

15–20 Oct

$7,142 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

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Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed, 1 bathroom

1–6 Oct

$1,301 SGD for 5 nights

4.98 out of 5 average rating, 40 reviews

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Top guest favourite

Cottage in Islesboro

"The Dory" on Penobscot Bay, Mid-Coast Maine

2 bedrooms, 3 beds, 1 bathroom

7–12 Oct

$2,261 SGD for 5 nights

5.0 out of 5 average rating, 42 reviews

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Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds, 2.5 bathrooms

1–6 Oct

$3,195 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Cottage in Islesboro

Sweet, three bedroom cape on peaceful cove

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

$2,535 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 41 reviews