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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, 47 reviews
Top 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, 8 reviews
Top guest favourite
Room in Peaks Island
Island Room with a View
1 double bed, 1 bathroom
18–23 Aug
4.97 out of 5 average rating, 109 reviews
Cottage in Long Island
Long Island Cottage: The Lobster Trap
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds, 1 bathroom
22–27 Oct
4.99 out of 5 average rating, 224 reviews
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 31 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, 78 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
Guest favourite
Place to stay in Peaks Island
Peaks Island stays with 2 night minimum
1 bedroom, 2 queen beds, 1 bathroom
31 Aug – 5 Sept
4.85 out of 5 average rating, 255 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
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 13 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Home in Portland
Ocean Paradise Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Aug
5.0 out of 5 average rating, 84 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
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
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
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, 11 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 195 reviews