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Search results; Over 1,000 homes in Peaks Island, Portland
Over 1,000 homes in Peaks Island, Portland
Top guest favourite
Guest favourite
Room in Peaks Island
Island Room with a View
1 bedroom
,
·
1 bed
,
·
1 shared bathroom
18–23 Aug
18–23 Aug
$1,543 SGD
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for 5 nights
$1,543 SGD for 5 nights
,
·
4.97 out of 5 average rating, 109 reviews
4.97 (109)
Guest favourite
Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed
1 bed
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,162 SGD
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for 5 nights
$1,162 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom
1 bedroom
,
·
2 beds
2 beds
19–24 Oct
19–24 Oct
$1,344 SGD
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for 5 nights
$1,344 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 222 reviews
4.99 (222)
Guest favourite
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$1,764 SGD
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for 5 nights
$1,764 SGD for 5 nights
4.97 out of 5 average rating, 30 reviews
4.97 (30)
Top guest favourite
Guest favourite
Home in Portland
Ocean View Cottage on Peaks Island
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
4–9 Sept
4–9 Sept
$4,221 SGD
$3,689 SGD
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for 5 nights
5.0 out of 5 average rating, 78 reviews
5.0 (78)
Top guest favourite
Guest favourite
Room in Portland
Baxter’s Place: Private room; sleeps 2
1 queen bed
1 queen bed
21–26 Aug
21–26 Aug
$1,500 SGD
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for 5 nights
$1,500 SGD for 5 nights
4.93 out of 5 average rating, 30 reviews
4.93 (30)
Guest favourite
Guest favourite
Room in Peaks Island
Peaks Islnd Charming xtra lng dbl-Harborside
1 bed
1 bed
9–14 Aug
9–14 Aug
$2,027 SGD
$1,706 SGD
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for 5 nights
4.8 out of 5 average rating, 122 reviews
4.8 (122)
Top guest favourite
Guest favourite
Home in Portland
The Island House
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
9–14 Aug
9–14 Aug
$5,541 SGD
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for 5 nights
$5,541 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favourite
Guest favourite
Cottage in Portland
Artist's Retreat
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
1–6 Jan
1–6 Jan
$2,408 SGD
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for 5 nights
$2,408 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 164 reviews
4.84 (164)
Top guest favourite
Guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,836 SGD
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for 5 nights
$3,836 SGD for 5 nights
5.0 out of 5 average rating, 70 reviews
5.0 (70)
Guest favourite
Guest favourite
Home in Portland
Island Treasure
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
16–21 Sept
16–21 Sept
$1,874 SGD
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for 5 nights
$1,874 SGD for 5 nights
4.85 out of 5 average rating, 136 reviews
4.85 (136)
Superhost
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
6–13 Sept
6–13 Sept
$2,998 SGD
$2,500 SGD
Show price breakdown
for 7 nights
Superhost
Superhost
Home in Portland
Summertime
1 bedroom
1 bedroom
,
·
3 beds
3 beds
16–23 Aug
16–23 Aug
$2,876 SGD
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for 7 nights
$2,876 SGD for 7 nights
Guest favourite
Guest favourite
Cottage in Portland
Peaks Island Waterfront
1 bedroom
1 bedroom
,
·
1 double bed
1 double bed
1–6 Jan
1–6 Jan
$2,685 SGD
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for 5 nights
$2,685 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 121 reviews
4.93 (121)
Top guest favourite
Guest favourite
Guest house in Portland
Tiny Cottage Hideaway, close to everything
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
14–19 Sept
14–19 Sept
$1,727 SGD
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for 5 nights
$1,727 SGD for 5 nights
4.97 out of 5 average rating, 174 reviews
4.97 (174)
Guest favourite
Guest favourite
Cabin in Portland
Sequester on Peaks Island
1 bedroom
1 bedroom
,
·
2 beds
2 beds
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,680 SGD
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for 5 nights
$1,680 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Apartment in Portland
Cozy Coveside Island Retreat
2 bedrooms
2 bedrooms
,
·
2 single beds
2 single beds
26–31 Aug
26–31 Aug
$2,130 SGD
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for 5 nights
$2,130 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Guest house in Yarmouth
Private Guesthouse in the Woods
1 bedroom
1 bedroom
,
·
2 beds
2 beds
19–24 Oct
19–24 Oct
$1,571 SGD
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for 5 nights
$1,571 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 216 reviews
4.99 (216)
Guest favourite
Guest favourite
Flat in Portland
Peaks Island Casco Bay View Condo w/ Beach Access
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$4,438 SGD
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for 5 nights
$4,438 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
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