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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

$2,630 SGD for 5 nights

,

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

$1,049 SGD for 5 nights

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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

$3,773 SGD for 5 nights

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5.0 out of 5 average rating, 110 reviews

Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed, 1 bathroom

8–13 Aug

$1,319 SGD for 5 nights

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4.97 out of 5 average rating, 38 reviews

Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds, 1 bathroom

19–24 Aug

$2,589 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 34 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds, 1 bathroom

23–30 Aug

$6,387 SGD for 7 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds, 3.5 bathrooms

7–12 Sept

$5,830 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds, 5 bathrooms

24–29 Aug

$15,471 SGD for 5 nights

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5.0 out of 5 average rating, 8 reviews

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds, 2 bathrooms

11–16 Sept

$4,382 SGD for 5 nights

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Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds, 2.5 bathrooms

22–27 Jul

$2,173 SGD for 5 nights

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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

$3,466 SGD for 5 nights

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Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds, 2 bathrooms

17–24 Aug

$5,869 SGD for 7 nights

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Free cancellation

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

$3,316 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds, 2 bathrooms

7–12 Sept

$7,215 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Northport

Cozy Coastal Cottage over Penobscot Bay!#ThinkFall

3 bedrooms, 4 beds, 1 bathroom

18–23 Sept

$2,096 SGD for 5 nights

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5.0 out of 5 average rating, 13 reviews

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds, 3 bathrooms

21–26 Aug

$3,239 SGD for 5 nights

Free cancellation

Home in Islesboro

Island Home

5 bedrooms, 6 beds, 2.5 bathrooms

15–22 Aug

$5,716 SGD for 7 nights

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Top guest favourite

Flat in Lincolnville

Ashgrove Garden on the Ocean

1 bedroom, 1 queen bed, 1 bathroom

24–29 Oct

$1,029 SGD for 5 nights

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4.99 out of 5 average rating, 68 reviews

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds, 3 bathrooms

9–15 Aug

$6,021 SGD for 6 nights

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Free cancellation