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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

27 Sept – 2 Oct

£2,334 total

,

5.0 out of 5 average rating, 113 reviews

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds

11–16 Sept

Free cancellation

Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 6 beds

13–20 Sept

£2,099 total

5.0 out of 5 average rating, 10 reviews

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds

6–11 Sept

£7,450 total

Free cancellation

5.0 out of 5 average rating, 9 reviews

Guest favourite

Cottage in Islesboro

Sweet, three bedroom cape on peaceful cove

3 bedrooms, 3 beds

9–14 Sept

£1,604 total

Free cancellation

4.92 out of 5 average rating, 39 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds

7–12 Sept

£2,763 total

5.0 out of 5 average rating, 13 reviews

Guest favourite

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds

22–27 Sept

£4,457 total

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed

16–21 Oct

Free cancellation

4.97 out of 5 average rating, 65 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds

7–12 Sept

£1,442 total

5.0 out of 5 average rating, 12 reviews

Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds

1–8 Sept

£3,631 total

Free cancellation

4.86 out of 5 average rating, 21 reviews

Guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds

7–12 Sept

£3,607 total

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Cottage in Islesboro

"The Dory" on Penobscot Bay, Mid-Coast Maine

2 bedrooms, 3 beds

5–10 Sept

£1,371 total

5.0 out of 5 average rating, 40 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds

5–12 Sept

£3,848 total

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds

1–6 Sept

£2,924 total

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds

1–6 Sept

£1,627 total

5.0 out of 5 average rating, 22 reviews

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds

1–6 Sept

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds

1–6 Dec

£2,051 total

4.88 out of 5 average rating, 8 reviews

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds

9–14 Sept

£3,005 total

Free cancellation

Flat in Islesboro

The Roost

1 bedroom, 2 beds

15–20 Sept

£1,142 total

Free cancellation