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Search results; Over 1,000 homes in Islesboro

Top guest favorite
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 favorite
Guesthouse in Islesboro
Milk House
1 queen bed, 1 bath
Sep 11 – 16
4.97 out of 5 average rating, 64 reviews
Guest favorite
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
Guest favorite
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
Top guest favorite
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
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
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
Top guest favorite
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 favorite
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
The Anchorage
4 bedrooms, 5 beds, 2 baths
Sep 11 – 16
Top guest favorite
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
Guest favorite
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
Guest favorite
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
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
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 baths
Aug 22 – 29
Apartment in Islesboro
The Roost
1 bedroom, 2 beds, 1 bath
Aug 15 – 20
New place to stay
Guest favorite
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
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 baths
Aug 16 – 22
Guest favorite
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