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Search results; Over 1,000 homes in Portland

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Top guest favourite
Flat in Portland
Penthouse Two Master Waterfront Suite with Rooftop
2 bedrooms, 2 beds, 2.5 private bathrooms
29 Oct – 3 Nov
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4.97 out of 5 average rating, 155 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, 179 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
25–30 Oct
4.96 out of 5 average rating, 380 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
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, 88 reviews
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Guest favourite
Home in Westbrook
Cozy Maine Cottage • Near Jetport & Coast
3 bedrooms, 3 queen beds, 2 bathrooms
8–13 Nov
4.89 out of 5 average rating, 649 reviews
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Guest favourite
Hotel room in Portland
Steps to Old Port | Hostel Bed in 8-Bed Coed Dorm
1 bedroom, 4 bunk beds, 3.5 bathrooms
18–23 Oct
4.92 out of 5 average rating, 230 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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Top guest favourite
Flat in Portland
AMAZING! Working waterfront views, 94 walk score!
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 394 reviews
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Top guest favourite
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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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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Superhost
Rooms in Portland
Two Historic Downtown King Rooms w/Private Bath
2 bedrooms, 2 king beds, 1 bathroom
25–30 Oct
New place to stay
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Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms, 5 beds, 1.5 bathrooms
18–23 Oct
4.86 out of 5 average rating, 206 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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Superhost
Flat in South Portland
The Perch at Willard Square-Elegant Beach Getaway
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Portland
Two Neighboring Units, 93 Walk Score, Sunny Patio!
6 bedrooms, 9 beds, 2 bathrooms
18–23 Oct
4.91 out of 5 average rating, 46 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
Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds, 2.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 305 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