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Search results; Over 1,000 homes in Islesboro

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Top guest favourite

Cottage in Islesboro

Islesboro Boathouse

1 bedroom, 1 bed, 1 private bathroom

27 Sept – 2 Oct

$3,159 SGD for 5 nights

,

5.0 out of 5 average rating, 115 reviews

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Top guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds

25–30 Sept

$4,293 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

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Guest favourite

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds

1–6 Dec

$3,184 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 9 reviews

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Guest favourite

Home in Islesboro

The Colony

2 bedrooms, 2 beds

18–23 Sept

5.0 out of 5 average rating, 6 reviews

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Guest favourite

Cottage in Islesboro

Ocean Front Island Cottage

2 bedrooms, 4 beds

22–27 Sept

$1,208 SGD for 5 nights

4.82 out of 5 average rating, 60 reviews

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Guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds

18–23 Sept

$3,956 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

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Home in Islesboro

Island Home

5 bedrooms, 6 beds

26 Sept – 3 Oct

$5,860 SGD for 7 nights

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Guest favourite

Home in Islesboro

Blue Moon Cottage

3 bedrooms, 4 beds

29 Sept – 6 Oct

Weekly discount

4.83 out of 5 average rating, 23 reviews

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Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed

16–21 Oct

Free cancellation

4.97 out of 5 average rating, 67 reviews

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Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds

28 Sept – 3 Oct

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds

19–24 Sept

$2,304 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

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Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds

21–26 Sept

5.0 out of 5 average rating, 42 reviews

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Home in Islesboro

The Anchorage

4 bedrooms, 5 beds

21–26 Sept

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Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds

26 Sept – 1 Oct

$2,202 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

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Top guest favourite

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds

22–27 Sept

$7,120 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

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Top guest favourite

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds

18–23 Sept

$3,968 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

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Guest favourite

Cottage in Islesboro

Sweet, three bedroom cape on peaceful cove

3 bedrooms, 3 beds

21–26 Sept

$2,527 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 41 reviews

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Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds

21–26 Sept

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Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds

18–25 Sept

$4,913 SGD for 7 nights

4.86 out of 5 average rating, 22 reviews