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Search results; Over 1,000 homes in Portland

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Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 174 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
5.0 out of 5 average rating, 3 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, 84 reviews
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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 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 Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 74 reviews
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Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms, 10 beds, 3 bathrooms
27 Sept – 2 Oct
4.88 out of 5 average rating, 118 reviews
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Home in Portland
Little Island Cottage
3 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 34 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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Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms, 4 beds, 2 bathrooms
30 Nov – 5 Dec
4.97 out of 5 average rating, 301 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 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
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
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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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, 371 reviews
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Superhost
Flat in Portland
Prom Queen
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Oct
New place to stay
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Guest favourite
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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Flat in Portland
Charming Modern West End Gem
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.93 out of 5 average rating, 321 reviews
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Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
5.0 out of 5 average rating, 152 reviews