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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 bath
Aug 16–21
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5.0 out of 5 average rating, 113 reviews
Top guest favourite
Guesthouse in Islesboro
Milk House
1 queen bed, 1 bath
Sep 11–16
4.97 out of 5 average rating, 64 reviews
Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 bedrooms, 3 beds, 2 baths
Sep 9–14
4.92 out of 5 average rating, 39 reviews
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 baths
Sep 11–16
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms, 5 beds, 1 bath
Aug 27–Sep 1
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms, 6 beds, 1.5 baths
Sep 13–20
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms, 3 beds, 1 bath
Sep 7–12
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 baths
Sep 7–12
5.0 out of 5 average rating, 11 reviews
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5 bedrooms, 8 beds, 5 baths
Aug 24–29
5.0 out of 5 average rating, 9 reviews
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 baths
Aug 14–19
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guesthouse in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 single beds, 1 bath
Aug 31–Sep 5
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Islesboro
Blue Moon Cottage
3 bedrooms, 4 beds, 1.5 baths
Aug 26–Sep 2
4.82 out of 5 average rating, 22 reviews
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms, 3 beds, 3 baths
Aug 21–26
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 baths
Sep 7–12
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Islesboro
Charming Seaside Island Retreat
5 bedrooms, 7 beds, 2 baths
Dec 1–6
4.83 out of 5 average rating, 6 reviews
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 baths
Aug 16–22
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 baths
Aug 23–30
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Tiny homes in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom, 1 sofa bed, 1 bath
Sep 27–Oct 2
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Islesboro
Newly built Scandinavian home
3 bedrooms, 3 beds, 2 baths
Sep 22–27
5.0 out of 5 average rating, 5 reviews