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Search results; Over 1,000 homes in Islesboro
Over 1,000 homes in Islesboro
Photo 1 of 17
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
,
·
1 bed
,
·
1 private bathroom
11–16 Oct
11–16 Oct
$3,156 SGD
Show price breakdown
for 5 nights
$3,156 SGD for 5 nights
,
·
5.0 out of 5 average rating, 116 reviews
5.0 (116)
Photo 1 of 22
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
16–21 Oct
16–21 Oct
$1,188 SGD
$1,035 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 68 reviews
4.97 (68)
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
13–18 Oct
13–18 Oct
$1,208 SGD
Show price breakdown
for 5 nights
$1,208 SGD for 5 nights
Free cancellation
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
1–6 Oct
1–6 Oct
$2,501 SGD
$2,011 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Top 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
1–6 Oct
1–6 Oct
$3,953 SGD
Show price breakdown
for 5 nights
$3,953 SGD for 5 nights
5.0 out of 5 average rating, 28 reviews
5.0 (28)
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
1–8 Oct
1–8 Oct
$1,473 SGD
$1,326 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
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Oct
1–6 Oct
$2,145 SGD
Show price breakdown
for 5 nights
$2,145 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
5–12 Sept
5–12 Sept
$3,507 SGD
Show price breakdown
for 7 nights
$3,507 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Photo 1 of 29
Home in Islesboro
Island Home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
3–10 Oct
3–10 Oct
$5,562 SGD
Show price breakdown
for 7 nights
$5,562 SGD for 7 nights
Photo 1 of 29
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
10–15 Oct
10–15 Oct
$4,208 SGD
$3,787 SGD
Show price breakdown
for 5 nights
Free cancellation
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
1–6 Oct
1–6 Oct
$4,290 SGD
Show price breakdown
for 5 nights
$4,290 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
15–20 Oct
15–20 Oct
$7,115 SGD
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for 5 nights
$7,115 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 27
Cabin in Islesboro
Maine Island Cabin, seaside gem
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
31 Jul – 5 Aug
31 Jul – 5 Aug
$1,501 SGD
Show price breakdown
for 5 nights
$1,501 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
$3,182 SGD
Show price breakdown
for 5 nights
$3,182 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
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
1–6 Oct
1–6 Oct
$2,500 SGD
$2,200 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
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
1–6 Oct
1–6 Oct
$2,525 SGD
Show price breakdown
for 5 nights
$2,525 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 41 reviews
4.93 (41)
Photo 1 of 8
Top guest favourite
Guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom
1 bedroom
,
·
1 sofa bed
1 sofa bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,296 SGD
Show price breakdown
for 5 nights
$1,296 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 40 reviews
4.98 (40)
Photo 1 of 29
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
$4,714 SGD
$4,172 SGD
Show price breakdown
for 5 nights
Free cancellation
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
1–6 Oct
1–6 Oct
$3,183 SGD
Show price breakdown
for 5 nights
$3,183 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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