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Search results; Over 1,000 homes in Islesboro

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 beds, 1 private bathroom
20–25 Jul
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5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Islesboro
Milk House
1 queen bed, 1 bathroom
30 Jul – 4 Aug
4.96 out of 5 average rating, 54 reviews
Home in Islesboro
Historic cottage with Penobscot Bay views
5 bedrooms, 7 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Islesboro
Driftwood deck overlooking a private pond
3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 111 reviews
Guest favourite
Cottage in Islesboro
1880s cottage with 180° bay views
4 bedrooms, 5 beds, 1 bathroom
23–30 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms, 6 beds, 1.5 bathrooms
13–20 Sept
5.0 out of 5 average rating, 7 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, 38 reviews
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5 bedrooms, 8 beds, 5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Tiny home in Islesboro
Island cottage with meadow views from deck
1 bedroom, 1 sofa bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Islesboro
Restored Victorian cottage on the ocean
5 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 26 reviews
Home in Islesboro
Oceanfront with 2 private beaches and dock
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Home in Islesboro
Post-and-beam home with dock on water
3 bedrooms, 3 beds, 3 bathrooms
21–26 Aug
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
9–15 Aug
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
17–24 Aug
4.86 out of 5 average rating, 21 reviews
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, 4 reviews
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Jul