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Search results; Over 1,000 homes in Portland

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Guest favourite
Cottage in Portland
Porches @ Peaks Island
3 bedrooms, 3 beds, 1.5 private bathrooms
28 Sept – 3 Oct
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4.87 out of 5 average rating, 68 reviews
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Guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds
25–30 Oct
4.97 out of 5 average rating, 67 reviews
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Top guest favourite
Flat in Portland
Charming Modern West End Gem
2 bedrooms, 2 beds
8–13 Nov
4.93 out of 5 average rating, 326 reviews
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Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest house in Harpswell
The Bird House
2 bedrooms, 2 beds
21–26 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms, 2 queen beds
2–7 Nov
4.96 out of 5 average rating, 226 reviews
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Guest favourite
Guest house in Falmouth
Garden Guesthouse in Falmouth, 5 mins to Portland
1 bedroom, 2 king beds
17–22 Sept
5.0 out of 5 average rating, 9 reviews
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Luxe
Apartment in Portland
Waterfront Two Master Suite Penthouse with Rooftop
2 bedrooms, 2 king beds
1–6 Nov
4.96 out of 5 average rating, 256 reviews
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Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds
12–17 Oct
4.96 out of 5 average rating, 178 reviews
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Top guest favourite
Guest suite in South Portland
Oceanfront with amazing views and private entrance
1 bedroom, 1 queen bed
2–7 Dec
4.99 out of 5 average rating, 905 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
4.95 out of 5 average rating, 377 reviews
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Guest favourite
Room in Portland
Large, spacious, and eclectic Room, Private Bath
1 queen bed
15–20 Nov
4.89 out of 5 average rating, 766 reviews
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Top guest favourite
Home in Portland
Historic Carriage House just steps from Casco Bay!
1 bedroom, 1 king bed
30 Oct – 4 Nov
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Portland
East End Unit
1 bedroom, 2 beds
7–12 Nov
4.94 out of 5 average rating, 191 reviews
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Top guest favourite
Home in South Portland
The Garden House - Studio w/private entrance
1 bedroom, 1 bed
11–16 Oct
5.0 out of 5 average rating, 49 reviews
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Superhost
Room in Portland
The Hope Island Room in Historic Downtown-Old Port
1 king bed
25–30 Oct
New place to stay
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Top guest favourite
Room in Portland
Waterview loft w/balcony/king/pr bath/spacious
1 king bed
18–23 Oct
4.97 out of 5 average rating, 368 reviews
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Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 86 reviews
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Top guest favourite
Guest suite in Portland
PRlVATE SUlTE in the Heart of East End Portland
1 bedroom, 1 double bed
30 Oct – 4 Nov
4.97 out of 5 average rating, 760 reviews