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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 bathroom
26–31 Oct
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5.0 out of 5 average rating, 109 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
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom, 2 single beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 18 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, 10 reviews
Home in Islesboro
The Anchorage
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5 bedrooms, 8 beds, 5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms, 7 beds, 3.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Islesboro
Island Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 8 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
Classic Maine Island Retreat
4 bedrooms, 7 beds, 2.5 bathrooms
3–8 Jul
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
Home in Islesboro
Island Home
5 bedrooms, 6 beds, 2.5 bathrooms
15–22 Aug
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms, 7 beds, 2 bathrooms
5–12 Jul
4.85 out of 5 average rating, 20 reviews
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms, 5 beds, 3 bathrooms
4–10 Jul
Home in Islesboro
Charming New England Summer Barn - on an island
4 bedrooms, 6 beds, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Islesboro
Islesboro Farmhouse
5 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Home in Northport
Double On The Rocks, ocean view family retreat
7 bedrooms, 9 beds, 4 bathrooms
22–27 Oct
5.0 out of 5 average rating, 17 reviews
Cottage in Islesboro
Windows By The Sea
4 bedrooms, 6 beds, 1.5 bathrooms
14–21 Nov
5.0 out of 5 average rating, 8 reviews
Superhost
Cabin in Lincolnville
Queen bed cabin, The Anchorage 11
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 4 reviews