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Search results; Over 1,000 homes in Portland

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Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 private bathroom
20–25 Sept
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5.0 out of 5 average rating, 74 reviews
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Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.96 out of 5 average rating, 55 reviews
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Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
New place to stay
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Home in Portland
Modern Portland House - Minutes to the Old Port!
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 16 reviews
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Flat in South Portland
Stylish New Apartment Near Willard Beach w/ Yard
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 83 reviews
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Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
18–23 Sept
4.97 out of 5 average rating, 174 reviews
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Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 39 reviews
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Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 23 reviews
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Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 87 reviews
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Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 16 reviews
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Home in Portland
Easy Old Port Access & Casco Bay View Craftsman
6 bedrooms, 10 beds, 3 bathrooms
26–31 Oct
4.97 out of 5 average rating, 264 reviews
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Flat in Portland
Glorious Getaway on the Eastern Promenade
2 bedrooms, 5 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 650 reviews
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Home in Portland
Ocean Paradise Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 85 reviews
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Home in Falmouth
Falmouth Foreside living
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 reviews
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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, 41 reviews
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Guest suite in Portland
Sunset Suite 42
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 238 reviews
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Flat in Portland
Old Port Artist Loft • Free Parking • Spacious 3BR
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 185 reviews
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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, 36 reviews
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Home in Windham
Lakehouse on Highland Lake
4 bedrooms, 8 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 88 reviews