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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
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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
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
4.97 out of 5 average rating, 68 reviews
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Guest favourite
Cottage in Islesboro
Ocean Front Island Cottage
2 bedrooms, 4 beds, 1 bathroom
13–18 Oct
4.82 out of 5 average rating, 60 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
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
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Islesboro
Blue Moon Cottage
3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Oct
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
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Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
10–15 Oct
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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
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, 2 bathrooms
1–6 Dec
4.89 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Islesboro
Newly built Scandinavian home
3 bedrooms, 3 beds, 2 bathrooms
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
1–8 Oct
4.86 out of 5 average rating, 22 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
5.0 out of 5 average rating, 42 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
4.93 out of 5 average rating, 41 reviews
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Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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
4.98 out of 5 average rating, 40 reviews
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Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct