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Search results; Over 1,000 homes in Portland

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Top guest favourite
Apartment in Portland
Charming, newly remodeled space atop Munjoy Hill.
1 bedroom, 1 bed, 1 private bathroom
17–22 Oct
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4.99 out of 5 average rating, 128 reviews
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Guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
2–7 Oct
4.96 out of 5 average rating, 178 reviews
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Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Portland
FABULOUS! Working waterfront views. 94 walk score.
6 bedrooms, 8 beds, 4 bathrooms
25–30 Oct
4.96 out of 5 average rating, 157 reviews
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Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms, 5 beds, 1.5 bathrooms
4–9 Oct
4.86 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Portland
Home in Portland
4 bedrooms, 9 beds, 1.5 bathrooms
11–16 Dec
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
18–23 Oct
4.95 out of 5 average rating, 58 reviews
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Guest favourite
Flat in Portland
Clean and Bright, Two Blocks to the Prom!
3 bedrooms, 3 queen beds, 1 bathroom
25–30 Oct
4.89 out of 5 average rating, 285 reviews
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Guest favourite
Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms, 10 beds, 3 bathrooms
29 Nov – 4 Dec
4.88 out of 5 average rating, 119 reviews
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Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
20–25 Oct
4.96 out of 5 average rating, 378 reviews
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Top guest favourite
Flat in Portland
Glorious Getaway on the Eastern Promenade
2 bedrooms, 5 beds, 1 bathroom
18–23 Oct
4.93 out of 5 average rating, 655 reviews
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Superhost
Rooms in Portland
c1800 Loft Downtown/Walk to Old Port
4 bedrooms, 6 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds, 2 bathrooms
6–11 Oct
5.0 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 86 reviews
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Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds, 2 bathrooms
11–16 Oct
4.95 out of 5 average rating, 43 reviews
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Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 77 reviews
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Top guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 157 reviews
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Top guest favourite
Flat in Portland
Modern Studio Loft w/ Parking in Perfect Location
1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.95 out of 5 average rating, 795 reviews