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Search results; Over 1,000 homes in Islesboro

Descriptions are based on details hosts provide
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, 111 reviews
Top guest favourite
Guest house in Islesboro
Vaulted ceilings and wood floors, Dark Harbor
4.96 out of 5 average rating, 54 reviews, 1 bed, 1 bathroom
30 Jul – 4 Aug
Home in Islesboro
Charming Seaside Island Retreat
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 2 bathrooms
8–13 Aug
Top guest favourite
Home in Islesboro
Island Retreat
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
5.0 out of 5 average rating, 19 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
Guest favourite
Cottage in Islesboro
1880s cottage with 180° bay views
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 1 bathroom
23–30 Aug
Guest favourite
Cottage in Islesboro
Surrounded by Water
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
13–20 Sept
Guest favourite
Villa in Islesboro
75-acre preserve with private oceanfront
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 8 beds, 5 bathrooms
24–29 Aug
Top guest favourite
Tiny home in Islesboro
Island cottage with meadow views from deck
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
5.0 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5.0 out of 5 average rating, 26 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms, 3 beds, 3 bathrooms
21–26 Aug
Home in Islesboro
Historic farmhouse on 22 wooded acres
4 bedrooms, 5 beds, 3 bathrooms
9–15 Aug
Home in Islesboro
Renovated farmhouse with a private beach
4.86 out of 5 average rating, 21 reviews, 4 bedrooms, 7 beds, 2 bathrooms
17–24 Aug
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
15–22 Aug
Home in Islesboro
New Scandinavian home with a private beach
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Jul
Home in Islesboro
Waterfront barn with Broad Cove views
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
22–27 Aug