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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

12–17 Jul

$1,531 SGD for 5 nights

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4.97 out of 5 average rating, 108 reviews

Superhost

Bed and breakfast in Portland

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

1 bedroom, 1 bed, 1 bathroom

30 Aug – 4 Sept

$1,180 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds, 1 bathroom

4–9 Oct

$1,590 SGD for 5 nights

4.99 out of 5 average rating, 220 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds, 2 bathrooms

29 Aug – 5 Sept

$8,307 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, 1 bathroom

10–15 Aug

$3,766 SGD for 5 nights

5.0 out of 5 average rating, 74 reviews

Top guest favourite

Cottage in Portland

Captain's Quarters on Peaks Island

1 bedroom, 1 bed, 1 bathroom

1–6 Jan

$2,363 SGD for 5 nights

4.98 out of 5 average rating, 40 reviews

Guest favourite

Holiday home in Portland

Heron's Perch on Peaks' Island

4 bedrooms, 8 beds, 2 bathrooms

25–30 Jul

$5,716 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Guest favourite

Home in Portland

Stunning Ocean Views From This Peaks Island Home

3 bedrooms, 5 beds, 2 bathrooms

30 Aug – 4 Sept

4.9 out of 5 average rating, 120 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed, 1 bathroom

30 Aug – 4 Sept

$2,782 SGD for 5 nights

4.93 out of 5 average rating, 118 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds, 1 bathroom

8–13 Sept

$1,840 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, 4 beds, 2 bathrooms

8–13 Oct

$5,736 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Flat in Portland

Peaks Island Casco Bay View Condo w/ Beach Access

2 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

$4,481 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds, 1 bathroom

27 Aug – 1 Sept

$3,988 SGD for 5 nights

5.0 out of 5 average rating, 68 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds, 2.5 bathrooms

8–15 Aug

$8,284 SGD for 7 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Home in Peaks Island

Peaks Island, Maine, Northcliffe Cottage

3 bedrooms, 5 beds, 1 bathroom

6–13 Sept

$3,369 SGD for 7 nights

4.83 out of 5 average rating, 18 reviews

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds, 1.5 bathrooms

6–11 Sept

$3,201 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Cottage in Portland

Spectacular Direct Oceanfront New Modern Home

3 bedrooms, 4 beds, 1 bathroom

1–8 Aug

$10,837 SGD for 7 nights

4.7 out of 5 average rating, 20 reviews

Guest favourite

Cabin in Portland

Sequester on Peaks Island

1 bedroom, 2 beds, 1 bathroom

13–18 Sept

$1,868 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Portland

Peaks Island Oceanfront Escape: Private Pool & A/C

4 bedrooms, 5 beds, 4.5 bathrooms

23–30 Aug

5.0 out of 5 average rating, 11 reviews