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Search results; Over 1,000 homes in Islesboro
Over 1,000 homes in Islesboro
Photo 1 of 22
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
Studio
,
·
1 bed
,
·
1 private bathroom
16–21 Oct
16–21 Oct
$1,190 SGD
$1,037 SGD
Show price breakdown
for 5 nights
,
·
4.97 out of 5 average rating, 67 reviews
4.97 (67)
Photo 1 of 17
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,163 SGD
Show price breakdown
for 5 nights
$3,163 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 115 reviews
5.0 (115)
Photo 1 of 23
Guest favourite
Guest favourite
Cottage in Islesboro
Ocean Front Island Cottage
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$1,209 SGD
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for 5 nights
$1,209 SGD for 5 nights
4.82 out of 5 average rating, 60 reviews
4.82 (60)
Photo 1 of 25
Guest favourite
Guest favourite
Home in Islesboro
The Colony
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
17–22 Sept
17–22 Sept
$2,506 SGD
$2,015 SGD
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for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
17–22 Sept
17–22 Sept
$3,962 SGD
Show price breakdown
for 5 nights
$3,962 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Islesboro
Charming Seaside Island Retreat
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
1–6 Dec
1–6 Dec
$3,189 SGD
Show price breakdown
for 5 nights
$3,189 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Photo 1 of 29
Home in Islesboro
Island Home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
26 Sept – 3 Oct
26 Sept – 3 Oct
$5,869 SGD
Show price breakdown
for 7 nights
$5,869 SGD for 7 nights
Photo 1 of 29
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$3,722 SGD
$3,251 SGD
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for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
18–23 Sept
18–23 Sept
$2,307 SGD
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for 5 nights
$2,307 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
24–29 Sept
24–29 Sept
$4,299 SGD
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for 5 nights
$4,299 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Islesboro
Newly built Scandinavian home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$7,131 SGD
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for 5 nights
$7,131 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Islesboro
Blue Moon Cottage
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
29 Sept – 6 Oct
29 Sept – 6 Oct
$1,476 SGD
$1,329 SGD
Show price breakdown
for 7 nights
Weekly discount
4.83 out of 5 average rating, 23 reviews
4.83 (23)
Photo 1 of 29
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$4,218 SGD
$3,796 SGD
Show price breakdown
for 5 nights
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$2,485 SGD
$2,193 SGD
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for 5 nights
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Photo 1 of 15
Guest favourite
Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,531 SGD
Show price breakdown
for 5 nights
$2,531 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 41 reviews
4.93 (41)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
17–22 Sept
17–22 Sept
$3,985 SGD
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for 5 nights
$3,985 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
$5,440 SGD
$4,808 SGD
Show price breakdown
for 5 nights
Photo 1 of 29
Top guest favourite
Guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom
1 bedroom
,
·
2 single beds
2 single beds
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,205 SGD
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for 5 nights
$2,205 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Photo 1 of 20
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
17–24 Sept
17–24 Sept
$4,920 SGD
Show price breakdown
for 7 nights
$4,920 SGD for 7 nights
4.86 out of 5 average rating, 22 reviews
4.86 (22)
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