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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

9–14 Aug

$1,532 SGD for 5 nights

,

4.97 out of 5 average rating, 109 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds, 1 bathroom

19–24 Oct

$1,372 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 221 reviews

Guest favourite

Room in Portland

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

1 bed, 1 bathroom

30 Aug – 4 Sept

$1,162 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Portland

Ocean View Cottage on Peaks Island

2 bedrooms, 3 beds, 1 bathroom

4–9 Sept

5.0 out of 5 average rating, 77 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed, 1 bathroom

4–9 Oct

$2,688 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 120 reviews

Guest favourite

Home in Long Island

Whole house on a great island in Casco Bay!

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,309 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 76 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$1,766 SGD for 5 nights

4.96 out of 5 average rating, 28 reviews

Guest favourite

Home in Portland

Island Treasure

3 bedrooms, 3 beds, 2 bathrooms

19–24 Sept

$1,877 SGD for 5 nights

4.87 out of 5 average rating, 134 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds, 2 bathrooms

19–26 Sept

$8,239 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds, 1 bathroom

30 Aug – 4 Sept

$3,841 SGD for 5 nights

5.0 out of 5 average rating, 70 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds, 2.5 bathrooms

28 Aug – 2 Sept

$5,528 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Cottage in Portland

Artist's Retreat

2 bedrooms, 2 queen beds, 1 bathroom

1–6 Jan

$1,816 SGD for 5 nights

Free cancellation

4.84 out of 5 average rating, 164 reviews

Guest favourite

Cabin in Portland

Sequester on Peaks Island

1 bedroom, 2 beds, 1 bathroom

29 Aug – 3 Sept

$1,682 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Holiday home in Portland

Heron's Perch on Peaks' Island

4 bedrooms, 8 beds, 2 bathrooms

7–12 Sept

$5,521 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Guest favourite

Home in Portland

Peaks Island Oceanfront Escape: Private Pool & A/C

4 bedrooms, 5 beds, 4.5 bathrooms

6–11 Sept

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Yurt in Chebeague Island

Yurt on Chebeague Island

1 bedroom, 1 queen bed, 1 bathroom

30 Aug – 4 Sept

$1,217 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 195 reviews

Guest favourite

Home in Portland

Stunning Ocean Views From This Peaks Island Home

3 bedrooms, 5 beds, 2 bathrooms

27 Oct – 1 Nov

4.9 out of 5 average rating, 122 reviews

Top guest favourite

Cottage in Portland

Captain's Quarters on Peaks Island

1 bedroom, 1 bed, 1 bathroom

1–6 Jan

$2,344 SGD for 5 nights

4.98 out of 5 average rating, 40 reviews

Home in Long Island

500Island

4 bedrooms, 5 beds, 2.5 bathrooms

23–30 Aug

$10,950 SGD for 7 nights

Free cancellation

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