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Search results; Over 1,000 homes in Islesboro

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
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
Top guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom, 1 sofa bed, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 38 reviews
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms, 5 beds, 1 bathroom
23–30 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 34 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
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 26 reviews
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 8 reviews
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Jul
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
Charming Seaside Island Retreat
5 bedrooms, 7 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Northport
Cozy Coastal Cottage over Penobscot Bay!#ThinkFall
3 bedrooms, 4 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 13 reviews
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
3+ Bedroom on the water with dock.
3 bedrooms, 3 beds, 3 bathrooms
21–26 Aug
Superhost
Home in Islesboro
Islesboro Farmhouse
5 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Flat in Lincolnville
Ashgrove Garden on the Ocean
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 68 reviews
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
15–22 Aug