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Search results; Over 1,000 homes in Islesboro

Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 beds, 1 private bathroom
9–14 Sept
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5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 114 reviews
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms, 5 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 26 reviews
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
19–26 Sept
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
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms, 6 beds, 1.5 bathrooms
20–27 Jun
5.0 out of 5 average rating, 10 reviews
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, 5 reviews
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
Guest favourite
Home in Islesboro
Blue Moon Cottage
3 bedrooms, 4 beds, 1.5 bathrooms
20–27 Sept
4.82 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 15 reviews
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
8–15 Sept
4.86 out of 5 average rating, 22 reviews
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
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms, 3 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Islesboro
Charming New England Summer Barn - on an island
4 bedrooms, 6 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 17 reviews
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
11–16 Sept
Top guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom, 1 sofa bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 39 reviews