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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

26–31 Jul

$1,550 SGD for 5 nights

,

4.97 out of 5 average rating, 108 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds

19–24 Oct

$1,367 SGD for 5 nights

4.99 out of 5 average rating, 221 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds

19–26 Sept

$8,302 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Portland

Ocean View Cottage on Peaks Island

2 bedrooms, 3 beds

10–15 Aug

$3,764 SGD for 5 nights

5.0 out of 5 average rating, 75 reviews

Superhost

Room in Portland

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

1 bed

30 Aug – 4 Sept

$1,171 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

$1,780 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Guest favourite

Holiday home in Portland

Heron's Perch on Peaks' Island

4 bedrooms, 8 beds

20–25 Sept

$5,713 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed

30 Aug – 4 Sept

$2,709 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 118 reviews

Guest favourite

Home in Portland

Stunning Ocean Views From This Peaks Island Home

3 bedrooms, 5 beds

27 Oct – 1 Nov

4.9 out of 5 average rating, 122 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds

27 Aug – 1 Sept

$3,985 SGD for 5 nights

5.0 out of 5 average rating, 69 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds

12–17 Sept

$5,505 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Home in Portland

Modern Peaks Island Getaway | Ocean Views + Decks

2 bedrooms, 3 beds

21–26 Nov

$3,271 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Portland

Island Treasure

3 bedrooms, 3 beds

22–27 Aug

$1,891 SGD for 5 nights

4.86 out of 5 average rating, 133 reviews

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds

6–11 Sept

$3,199 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Cottage in Portland

Spectacular Direct Oceanfront New Modern Home

3 bedrooms, 4 beds

1–8 Aug

$10,551 SGD for 7 nights

4.7 out of 5 average rating, 20 reviews

Top guest favourite

Guest house in Portland

Tiny Cottage Hideaway, close to everything

1 bedroom, 1 queen bed

30 Aug – 4 Sept

$1,629 SGD for 5 nights

4.96 out of 5 average rating, 170 reviews

Top guest favourite

Home in Portland

The Island House

3 bedrooms, 5 beds

9–14 Aug

$5,615 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Peaks Island

Peaks Island, Maine, Northcliffe Cottage

3 bedrooms, 5 beds

6–13 Sept

$3,367 SGD for 7 nights

Free cancellation

4.83 out of 5 average rating, 18 reviews

Guest favourite

Home in Portland

Peaks Island Oceanfront Escape: Private Pool & A/C

4 bedrooms, 5 beds

23–30 Aug

5.0 out of 5 average rating, 12 reviews