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

Top guest favourite

Flat in Peaks Island

Beach Front, Waterfront, Ferry Beach

2 bedrooms, 3 beds, 1 private bathroom

7–12 Sept

$3,842 SGD for 5 nights

,

5.0 out of 5 average rating, 45 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds

19–24 Oct

$1,395 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 221 reviews

Superhost

Room in Portland

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

1 bed

30 Aug – 4 Sept

$1,175 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed

4–9 Oct

$2,702 SGD for 5 nights

Pay $0 today

Free cancellation

4.93 out of 5 average rating, 120 reviews

Top guest favourite

Room in Peaks Island

Island Room with a View

1 double bed

9–14 Aug

$1,526 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 109 reviews

Top guest favourite

Home in Portland

Ocean View Cottage on Peaks Island

2 bedrooms, 3 beds

4–9 Sept

Free cancellation

5.0 out of 5 average rating, 76 reviews

Guest favourite

Home in Long Island

Whole house on a great island in Casco Bay!

3 bedrooms, 4 beds

7–12 Sept

$4,330 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 76 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds

28 Aug – 2 Sept

$5,555 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 26 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds

16–21 Aug

$1,775 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 27 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds

19–26 Sept

$8,280 SGD for 7 nights

Free cancellation

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

27 Aug – 1 Sept

$3,975 SGD for 5 nights

5.0 out of 5 average rating, 70 reviews

Guest favourite

Home in Portland

Island Treasure

3 bedrooms, 3 beds

19–24 Sept

$1,886 SGD for 5 nights

Free cancellation

4.87 out of 5 average rating, 134 reviews

Home in Long Island

500Island

4 bedrooms, 5 beds

23–30 Aug

$11,004 SGD for 7 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Home in Portland

The Island House

3 bedrooms, 5 beds

9–14 Aug

$5,600 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds

6–11 Sept

$3,191 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Room in Portland

Baxter’s Place: Private room; sleeps 2

1 queen bed

21–26 Aug

$1,523 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 29 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

Home in Portland

Modern Peaks Island Getaway | Ocean Views + Decks

2 bedrooms, 3 beds

29 Aug – 3 Sept

$4,968 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 9 reviews

Cottage in Portland

Spectacular Direct Oceanfront New Modern Home

3 bedrooms, 4 beds

7–12 Sept

$6,340 SGD for 5 nights

4.7 out of 5 average rating, 20 reviews