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
4.96 out of 5 average rating, 51 reviews, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Jul
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 8 beds, 5 bathrooms
5–10 Jul
Top guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Aug
Top guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
5–10 Jul
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
3–8 Jul
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
5.0 out of 5 average rating, 34 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
5.0 out of 5 average rating, 10 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, 7 beds, 1.5 bathrooms
13–20 Sept
Top guest favourite
Home in Islesboro
Island Retreat
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
4.92 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
4–10 Jul
Top guest favourite
Cottage in Northport
Cozy Coastal Cottage overlooking Bay. Think Fall!
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1 bathroom
18–23 Sept
Guest favourite
Home in Islesboro
"The Gables" on Penobscot Bay, Mid-Coast Maine
4.9 out of 5 average rating, 81 reviews, 3 bedrooms, 5 beds, 1 bathroom
9–14 Jul
Top guest favourite
Cottage in Northport
"Nestled Inn" Cottage - With Direct Water Access
4.93 out of 5 average rating, 28 reviews, 2 bedrooms, 2 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Lincolnville
Ashgrove Garden on the Ocean
4.99 out of 5 average rating, 68 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Top guest favourite
Home in Lincolnville
Antique Barn Apartment at Salt Water Farm
5.0 out of 5 average rating, 58 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept