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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
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,161 SGD
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for 5 nights
$1,161 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
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$1,300 SGD
Show price breakdown
for 5 nights
$1,300 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
,
·
1 bathroom
1 bathroom
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
The Island House
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
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)
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
,
·
1 bathroom
1 bathroom
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 Long Island
Whole house on a great island in Casco Bay!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$4,303 SGD
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for 5 nights
$4,303 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 76 reviews
4.99 (76)
Guest favourite
Guest favourite
Home in Portland
BELLA VISTA - DIRECT OCEANFRONT at Elm Cove
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Aug – 2 Sept
28 Aug – 2 Sept
$5,521 SGD
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for 5 nights
$5,521 SGD for 5 nights
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Home in Long Island
500Island
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
23–30 Aug
23–30 Aug
$10,936 SGD
Show price breakdown
for 7 nights
$10,936 SGD for 7 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,216 SGD
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for 5 nights
$1,216 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 195 reviews
4.98 (195)
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$6,301 SGD
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for 5 nights
$6,301 SGD for 5 nights
4.7 out of 5 average rating, 20 reviews
4.7 (20)
Top guest favourite
Guest favourite
Home in Portland
Ocean View Cottage on Peaks Island
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
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
Cottage in Portland
Captain's Quarters on Peaks Island
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Jan
1–6 Jan
$2,341 SGD
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for 5 nights
$2,341 SGD for 5 nights
4.98 out of 5 average rating, 40 reviews
4.98 (40)
Guest favourite
Guest favourite
Cottage in Portland
Peaks Island Waterfront
1 bedroom
1 bedroom
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
1–6 Jan
1–6 Jan
$2,685 SGD
Show price breakdown
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
Room in Portland
Baxter’s Place: Private room; sleeps 2
1 queen bed
1 queen bed
,
·
WC
WC
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)
Superhost
Superhost
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms
4 bedrooms
,
·
2 double beds
2 double beds
,
·
2 bathrooms
2 bathrooms
7–12 Oct
7–12 Oct
$4,670 SGD
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for 5 nights
$4,670 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,583 SGD
$3,959 SGD
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for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Home in Portland
Island Treasure
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
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)
Cottage in Portland
Dream Maine Cottage on Peaks Island
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Sept
9–14 Sept
$5,020 SGD
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for 5 nights
$5,020 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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