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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

21–26 Jun

$3,766 SGD for 5 nights

,

5.0 out of 5 average rating, 109 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed

11–16 Jul

$1,073 SGD for 5 nights

4.96 out of 5 average rating, 51 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds

26 Jun – 1 Jul

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 7 beds

12–19 Jul

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds

20–25 Jun

$2,625 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds

23–30 Aug

$6,375 SGD for 7 nights

5.0 out of 5 average rating, 9 reviews

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds

26 Jun – 1 Jul

$3,507 SGD for 5 nights

Top guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds

21–26 Jun

$5,819 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds

24–29 Jun

$13,388 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed

22–27 Jun

$1,316 SGD for 5 nights

4.97 out of 5 average rating, 37 reviews

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds

8–13 Aug

$3,309 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds

11–16 Sept

$4,374 SGD for 5 nights

Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds

7–12 Sept

$2,579 SGD for 5 nights

5.0 out of 5 average rating, 34 reviews

Guest favourite

Cottage in Islesboro

Sweet, three bedroom cape on peaceful cove

3 bedrooms, 3 beds

9–14 Sept

$2,587 SGD for 5 nights

4.92 out of 5 average rating, 37 reviews

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds

22–28 Jun

$6,010 SGD for 6 nights

Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds

19–26 Jun

$5,857 SGD for 7 nights

4.85 out of 5 average rating, 20 reviews

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds

21–26 Jun

$5,739 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Home in Islesboro

Charming New England Summer Barn - on an island

4 bedrooms, 6 beds

11–16 Jul

$3,233 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds

15–22 Aug

$5,705 SGD for 7 nights