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

Guest favourite
Home in Peaks Island
Panoramic Sea Views, Oceanic Hot Tub
3 bedrooms, 6 beds, 2.5 private bathrooms
16–23 Aug
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4.91 out of 5 average rating, 90 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, 5 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
Top guest favourite
Guest house in Portland
Tiny Cottage Hideaway, close to everything
1 bedroom, 1 queen bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 173 reviews
Guest favourite
Cottage in Portland
Peaks Island Waterfront
1 bedroom, 1 double bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 121 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
Room in Portland
Baxter’s Place: Private room; sleeps 2
1 queen bed, WC
21–26 Aug
4.93 out of 5 average rating, 30 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
Home in Portland
Ocean view cottage Peaks Island
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 20 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
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 Portland
Island Getaway, Short ferry ride to Portland
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 39 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
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
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
Superhost
Home in Portland
The Dwelling Place
2 bedrooms, 3 beds, 1 bathroom
23–30 Aug
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
Top guest favourite
Flat in Portland
Central-Local Studio in Vibrant Portland, Maine!
1 bedroom, 1 queen bed, 1 bathroom
23–28 Nov
4.9 out of 5 average rating, 461 reviews