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Search results; Over 1,000 homes in Portland

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Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds, 1 bathroom
22–27 Oct
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4.99 out of 5 average rating, 234 reviews
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Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds
2–7 Oct
4.96 out of 5 average rating, 179 reviews
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Guest favourite
Home in Westbrook
Cozy Maine Cottage • Near Jetport & Coast
3 bedrooms, 3 queen beds
8–13 Nov
4.89 out of 5 average rating, 649 reviews
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Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds
18–23 Oct
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Flat in Portland
FABULOUS! Working waterfront views. 94 walk score.
6 bedrooms, 8 beds
25–30 Oct
4.96 out of 5 average rating, 157 reviews
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Guest favourite
Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms, 10 beds
29 Nov – 4 Dec
4.88 out of 5 average rating, 119 reviews
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Top guest favourite
Flat in Portland
AMAZING! Working waterfront views, 94 walk score!
3 bedrooms, 4 beds
25–30 Oct
4.95 out of 5 average rating, 394 reviews
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Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Portland
Clean and Bright, Two Blocks to the Prom!
3 bedrooms, 3 queen beds
25–30 Oct
4.89 out of 5 average rating, 285 reviews
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Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds
20–25 Oct
4.96 out of 5 average rating, 379 reviews
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Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms, 5 beds
4–9 Oct
4.86 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds
26–31 Oct
5.0 out of 5 average rating, 86 reviews
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Top guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 157 reviews
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Top guest favourite
Flat in Portland
Glorious Getaway on the Eastern Promenade
2 bedrooms, 5 beds
18–23 Oct
4.93 out of 5 average rating, 655 reviews
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Superhost
Rooms in Portland
Two Historic Downtown King Rooms w/Private Bath
2 bedrooms, 2 king beds
25–30 Oct
New place to stay
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Top guest favourite
Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds
6–11 Oct
5.0 out of 5 average rating, 88 reviews
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Cottage in Portland
Cozy Renovated Home | Portland, ME
2 bedrooms, 2 beds
1–6 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Flat in South Portland
Stylish New Apartment Near Willard Beach w/ Yard
4 bedrooms, 5 beds
1–6 Nov
4.99 out of 5 average rating, 86 reviews
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Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Dec
4.98 out of 5 average rating, 90 reviews