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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

$3,769 SGD for 5 nights

,

5.0 out of 5 average rating, 110 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed

11–16 Sept

$1,074 SGD for 5 nights

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4.96 out of 5 average rating, 52 reviews

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds

20–25 Jul

$2,627 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds

2–7 Aug

$2,300 SGD for 5 nights

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5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds

23–30 Aug

$6,381 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds

8–13 Jul

$5,825 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds

22–27 Jul

$3,484 SGD for 5 nights

Free cancellation

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds

24–29 Aug

$15,456 SGD for 5 nights

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5.0 out of 5 average rating, 8 reviews

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds

8–13 Aug

$3,312 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds

11–16 Sept

$4,378 SGD for 5 nights

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Free cancellation

Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds

17–22 Aug

$2,582 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 34 reviews

Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed

8–13 Aug

$1,318 SGD for 5 nights

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4.97 out of 5 average rating, 38 reviews

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds

9–15 Aug

$6,015 SGD for 6 nights

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Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds

17–24 Aug

$5,863 SGD for 7 nights

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Free cancellation

4.86 out of 5 average rating, 21 reviews

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds

7–12 Sept

$7,401 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds

15–22 Aug

$5,711 SGD for 7 nights

Free cancellation

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds

21–26 Aug

$3,236 SGD for 5 nights

Free cancellation

Home in Islesboro

Charming New England Summer Barn - on an island

4 bedrooms, 6 beds

22–27 Aug

$2,856 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 15 reviews

Superhost

Cabin in Lincolnville

Queen bed cabin, The Anchorage 11

1 bedroom, 1 queen bed

8–13 Jul

$1,483 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews