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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
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5.0 out of 5 average rating, 46 reviews
Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.99 out of 5 average rating, 221 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
4.99 out of 5 average rating, 76 reviews
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Room in Peaks Island
Island Room with a View
1 double bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 109 reviews
Top guest favourite
Home in Portland
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Hotel in Portland
Portland’s only hotel with unobstructed bay views
1 bedroom, 1 double bed, 1 bathroom
16–21 Aug
4.87 out of 5 average rating, 182 reviews
Guest favourite
Cottage in Portland
Peaks Island Waterfront
1 bedroom, 1 double bed, 1 bathroom
1–6 Jan
4.93 out of 5 average rating, 121 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
5.0 out of 5 average rating, 70 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Superhost
Flat in Portland
Prom Queen
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Aug
New place to stay
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
Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
3 bedrooms, 5 beds, 1 bathroom
6–13 Sept
4.83 out of 5 average rating, 18 reviews
Superhost
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms, 2 double beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Portland
Captain's Quarters on Peaks Island
1 bedroom, 1 bed, 1 bathroom
1–6 Jan
4.98 out of 5 average rating, 40 reviews
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.7 out of 5 average rating, 20 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 9 reviews