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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
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5.0 out of 5 average rating, 115 reviews
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Top guest favourite
Guest house in Islesboro
Milk House
1 queen bed, 1 bathroom
16–21 Oct
4.97 out of 5 average rating, 67 reviews
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Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
26 Sept – 3 Oct
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Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 26 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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Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Islesboro
Newly built Scandinavian home
3 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms, 5 beds, 1 bathroom
24–29 Sept
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, 1 bathroom
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, 2 bathrooms
20–25 Sept
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Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
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
29 Sept – 6 Oct
4.83 out of 5 average rating, 23 reviews
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Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 41 reviews
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Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
17–24 Sept
4.86 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms, 3 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 single beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 23 reviews
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Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
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Top guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom, 1 sofa bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 40 reviews
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Guest favourite
Home in Islesboro
Charming New England Summer Barn - on an island
4 bedrooms, 6 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 17 reviews