We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Islesboro

Guest favourite

Guest house in Islesboro

Main Cabin at Coveside on Islesboro

2 bedrooms, 3 beds, 1 private bathroom

25–30 Aug

$3,604 SGD for 5 nights

,

4.92 out of 5 average rating, 39 reviews

Top guest favourite

Cottage in Islesboro

Islesboro Boathouse

1 bedroom, 1 bed, 1 bathroom

27 Sept – 2 Oct

$3,741 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 112 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed, 1 bathroom

16–21 Aug

$1,040 SGD for 5 nights

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 60 reviews

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 single beds, 1 bathroom

7–12 Aug

$2,607 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 20 reviews

Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed, 1 bathroom

9–14 Aug

$1,278 SGD for 5 nights

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 39 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds, 2.5 bathrooms

10–15 Aug

Free cancellation

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Islesboro

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

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

Free cancellation

5.0 out of 5 average rating, 37 reviews

Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 6 beds, 1.5 bathrooms

13–20 Sept

$3,363 SGD for 7 nights

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, 2 bathrooms

9–14 Sept

$2,570 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 39 reviews

Flat in Islesboro

The Roost

1 bedroom, 2 beds, 1 bathroom

1–6 Aug

$1,784 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds, 2 bathrooms

11–16 Sept

$4,345 SGD for 5 nights

Pay $0 today

Free cancellation

Flat in Islesboro

Coastal Island Escape

2 bedrooms, 3 beds, 1 bathroom

4–9 Aug

$1,892 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Home in Islesboro

Charming New England Summer Barn - on an island

4 bedrooms, 6 beds, 1.5 bathrooms

5–10 Sept

Free cancellation

5.0 out of 5 average rating, 15 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds, 1 bathroom

22–29 Aug

$5,849 SGD for 7 nights

5.0 out of 5 average rating, 12 reviews

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds, 2.5 bathrooms

14–19 Aug

$3,348 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds, 5 bathrooms

24–29 Aug

$15,340 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds, 3.5 bathrooms

7–12 Sept

$5,781 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds, 2 bathrooms

23–30 Aug

$5,819 SGD for 7 nights

Pay $0 today

Free cancellation

4.86 out of 5 average rating, 21 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds, 2.5 bathrooms

15–22 Aug

$5,743 SGD for 7 nights

Free cancellation