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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

£2,336 total

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5.0 out of 5 average rating, 113 reviews

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds, 2 bathrooms

11–16 Sept

Pay £0 today

Free cancellation

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds, 5 bathrooms

6–11 Sept

£7,455 total

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Free cancellation

5.0 out of 5 average rating, 9 reviews

Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 6 beds, 1.5 bathrooms

13–20 Sept

£2,100 total

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed, 1 bathroom

16–21 Oct

Pay £0 today

Free cancellation

4.97 out of 5 average rating, 65 reviews

Guest favourite

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds, 2 bathrooms

22–27 Sept

£4,460 total

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds, 2.5 bathrooms

7–12 Sept

£1,443 total

5.0 out of 5 average rating, 12 reviews

Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds, 2 bathrooms

1–8 Sept

£3,633 total

Pay £0 today

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, 3.5 bathrooms

7–12 Sept

£3,610 total

5.0 out of 5 average rating, 26 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds, 1 bathroom

7–12 Sept

£2,765 total

5.0 out of 5 average rating, 13 reviews

Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

£1,372 total

5.0 out of 5 average rating, 40 reviews

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds, 3 bathrooms

1–6 Sept

£2,926 total

5.0 out of 5 average rating, 4 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds, 2.5 bathrooms

5–12 Sept

£3,850 total

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds, 1 bathroom

1–6 Sept

£1,628 total

5.0 out of 5 average rating, 22 reviews

Flat in Islesboro

The Roost

1 bedroom, 2 beds, 1 bathroom

15–20 Sept

£1,142 total

Pay £0 today

Free cancellation

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds, 2.5 bathrooms

1–6 Sept

5.0 out of 5 average rating, 3 reviews

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds, 3 bathrooms

9–14 Sept

£3,007 total

Pay £0 today

Free cancellation

Guest favourite

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds, 2 bathrooms

1–6 Dec

£2,053 total

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Islesboro

Blue Moon Cottage

3 bedrooms, 4 beds, 1.5 bathrooms

9–14 Sept

£779 total

4.82 out of 5 average rating, 22 reviews