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Search results; Over 1,000 homes in Portland

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Top guest favourite
Loft in Portland
Downtown Penthouse Suite - Stunning Harbor Views
2 bedrooms, 2 beds, 2 private bathrooms
25–30 Oct
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4.97 out of 5 average rating, 324 reviews
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Flat in Portland
1-bedroom unit (3 beds) with free parking
1 bedroom, 3 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 154 reviews
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Top guest favourite
Guest house in Portland
Spacious & Convenient 2 Bd/1 bath w/ Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.96 out of 5 average rating, 522 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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Guest suite in Portland
Sunset Suite 42
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 242 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, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 760 reviews
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Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds, 1 bathroom
22–27 Oct
4.99 out of 5 average rating, 233 reviews
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Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Apr
5.0 out of 5 average rating, 40 reviews
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Flat in Portland
Peaceful Oasis on Munjoy Hill -2nd flr/3BR+parking
3 bedrooms, 4 beds, 1 bathroom
22–27 Nov
4.97 out of 5 average rating, 691 reviews
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Flat in Portland
Boutique BnB in The Heart of East End Portland!
2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.98 out of 5 average rating, 486 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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Barn in Portland
Garrison Cove Studio
1 bed, 1 bathroom
31 Oct – 5 Nov
5.0 out of 5 average rating, 498 reviews
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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, 155 reviews
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Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
18–23 Dec
4.98 out of 5 average rating, 90 reviews
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Home in Portland
Wall St. Retreat: Family-Ready Portland Home
3 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Old Orchard Beach
Luxury Home w/HOT TUB & Fire Pit
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 236 reviews
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Guest suite in Portland
Sunflower Retreat in North Back Cove
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 325 reviews
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Home in Portland
Historic Carriage House just steps from Casco Bay!
1 bedroom, 1 king bed, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 13 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