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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

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

30 Aug – 4 Sept

$1,162 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Portland

Tiny Cottage Hideaway, close to everything

1 bedroom, 1 queen bed

14–19 Sept

$1,729 SGD for 5 nights

4.97 out of 5 average rating, 173 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed

4–9 Oct

$2,688 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 121 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, 77 reviews

Top guest favourite

Room in Portland

Baxter’s Place: Private room; sleeps 2

1 queen bed

21–26 Aug

$1,510 SGD for 5 nights

4.93 out of 5 average rating, 30 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds

16–21 Aug

$1,766 SGD for 5 nights

4.96 out of 5 average rating, 28 reviews

Guest favourite

Home in Portland

Peaks Island Oceanfront Escape: Private Pool & A/C

4 bedrooms, 5 beds

6–11 Sept

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Portland

Island Treasure

3 bedrooms, 3 beds

19–24 Sept

$1,877 SGD for 5 nights

4.87 out of 5 average rating, 134 reviews

Top guest favourite

Flat in Peaks Island

Beach Front, Waterfront, Ferry Beach

2 bedrooms, 3 beds

7–12 Sept

$3,826 SGD for 5 nights

5.0 out of 5 average rating, 45 reviews

Guest favourite

Home in Portland

Island Getaway, Short ferry ride to Portland

1 bedroom, 1 queen bed

8–13 Sept

$2,090 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Guest favourite

Home in Long Island

Whole house on a great island in Casco Bay!

3 bedrooms, 4 beds

7–12 Sept

$4,309 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Home in Portland

Ocean view cottage Peaks Island

4 bedrooms, 5 beds

20–25 Sept

$4,460 SGD for 5 nights

5.0 out of 5 average rating, 20 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds

30 Aug – 4 Sept

$3,841 SGD for 5 nights

5.0 out of 5 average rating, 70 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

Home in Portland

Historic Island Retreat

2 bedrooms, 3 beds

1–6 Nov

$1,890 SGD for 5 nights

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds

6–11 Sept

$3,175 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Guest favourite

Cottage in Portland

Artist's Retreat

2 bedrooms, 2 queen beds

1–6 Jan

$1,816 SGD for 5 nights

Free cancellation

4.84 out of 5 average rating, 164 reviews