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Search results; Over 1,000 homes in Islesboro

Top guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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5.0 out of 5 average rating, 109 reviews
Top guest favourite
Guest house in Islesboro
Milk House
1 queen bed, 1 bathroom
11–16 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms, 7 beds, 1.5 bathrooms
12–19 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 single beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 18 reviews
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
1–6 Jul
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms, 5 beds, 1 bathroom
23–30 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5 bedrooms, 8 beds, 5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 24 reviews
Home in Islesboro
Charming Seaside Island Retreat
5 bedrooms, 7 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
5–12 Jul
4.85 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom, 1 sofa bed, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 37 reviews
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Home in Islesboro
Charming New England Summer Barn - on an island
4 bedrooms, 6 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
1–7 Jul
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
15–22 Aug
Home in Islesboro
Newly built Scandinavian home
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews