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Search results; Over 1,000 homes in Peaks Island, Portland

Top guest favourite

Room in Peaks Island

Island Room with a View

1 bedroom, 1 bed, 1 shared bathroom

7–12 Aug

$1,558 SGD for 5 nights

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4.97 out of 5 average rating, 108 reviews

Superhost

Room in Portland

Aerie 2 reg:STHR-007375-2025 Peaks Island, Me

1 bed

30 Aug – 4 Sept

$1,170 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds

16–21 Aug

$1,778 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds

19–24 Oct

$1,398 SGD for 5 nights

4.99 out of 5 average rating, 221 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds

28 Aug – 2 Sept

$5,566 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Room in Peaks Island

Cozy Island room in a charming home

1 double bed

2–7 Aug

$1,456 SGD for 5 nights

4.93 out of 5 average rating, 137 reviews

Guest favourite

Room in Portland

Baxter’s Place: Private room; sleeps 2

1 queen bed

1–6 Aug

$1,372 SGD for 5 nights

4.93 out of 5 average rating, 28 reviews

Top guest favourite

Home in Portland

Ocean View Cottage on Peaks Island

2 bedrooms, 3 beds

4–9 Sept

5.0 out of 5 average rating, 76 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed

30 Aug – 4 Sept

$2,707 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 118 reviews

Top guest favourite

Home in Portland

The Island House

3 bedrooms, 5 beds

9–14 Aug

$5,602 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds

27 Aug – 1 Sept

$3,982 SGD for 5 nights

5.0 out of 5 average rating, 69 reviews

Guest favourite

Home in Peaks Island

Peaks Island, Maine, Northcliffe Cottage

3 bedrooms, 5 beds

6–13 Sept

$3,364 SGD for 7 nights

Free cancellation

4.83 out of 5 average rating, 18 reviews

Top guest favourite

Home in Portland

Modern Peaks Island Getaway | Ocean Views + Decks

2 bedrooms, 3 beds

21–26 Nov

$3,223 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Home in Long Island

500Island

4 bedrooms, 5 beds

23–30 Aug

$11,025 SGD for 7 nights

Free cancellation

New place to stay

Cottage in Portland

Spectacular Direct Oceanfront New Modern Home

3 bedrooms, 4 beds

7–12 Sept

$6,352 SGD for 5 nights

4.7 out of 5 average rating, 20 reviews

Guest favourite

Home in Portland

Island Treasure

3 bedrooms, 3 beds

19–24 Sept

$1,890 SGD for 5 nights

4.86 out of 5 average rating, 133 reviews

Superhost

Home in Portland

Unbeatable view! Peaceful spot.

4 bedrooms, 2 double beds

7–12 Oct

$4,708 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds

19–26 Sept

$8,295 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Superhost

Home in Portland

Gull Cottage: A Classic Peaks Island Charmer

3 bedrooms, 4 beds

6–13 Sept