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

Top guest favourite
Room in Peaks Island
Cozy Island room in a charming home
1 bedroom, 1 bed, 1 shared bathroom
13–18 Sept
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4.94 out of 5 average rating, 141 reviews
Top guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 67 reviews
Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 86 reviews
Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 42 reviews
Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 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
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
8–14 Nov
5.0 out of 5 average rating, 38 reviews
Cottage in Portland
Dream Maine Cottage on Peaks Island
3 bedrooms, 8 beds, 1.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 5 reviews
Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 17 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, 229 reviews
Superhost
Home in Portland
Classic Charm, Ocean View
5 bedrooms, 7 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Room in Peaks island
Aerie Peaks Island registration STHR-007375-2025
1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Portland
Peaks Island Oceanfront Escape: Private Pool & A/C
4 bedrooms, 5 beds, 4.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Portland
The Dwelling Place
2 bedrooms, 3 beds, 1 bathroom
13–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 24 reviews
Flat in Portland
Cozy studio apartment high up in the woods.
2 bedrooms, 2 beds, No bathroom
9–14 Sept
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews