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Search results; Over 1,000 homes in Portland

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Top guest favourite
Flat in Portland
Urban Seaside Retreat- East End Overlook Casco Bay
1 bedroom, 1 bed, 1 private bathroom
29 Dec – 3 Jan
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4.98 out of 5 average rating, 166 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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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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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, 235 reviews
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Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 226 reviews
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Top guest favourite
Flat in Portland
Sophisticated Charm at an unbeatable price!
2 bedrooms, 2 beds, 1 bathroom
9–14 Nov
4.92 out of 5 average rating, 656 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, 86 reviews
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Top guest favourite
Place to stay in Portland
Top of Portland's Munjoy Hill
2 bedrooms, 2 beds, No bathroom
1–6 Dec
4.92 out of 5 average rating, 1253 reviews
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Top guest favourite
Cottage in Harpswell
Updated Historic Cottage, Private Waterfront, 5BR
5 bedrooms, 7 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 18 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
12–17 Oct
4.96 out of 5 average rating, 178 reviews
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Top guest favourite
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, 690 reviews
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Top guest favourite
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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Guest favourite
Guest house in Falmouth
Garden Guesthouse in Falmouth, 5 mins to Portland
1 bedroom, 2 king beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Portland
Fore River Getaway
3 bedrooms, 4 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 107 reviews
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Cottage in Portland
Cozy Renovated Home | Portland, ME
2 bedrooms, 2 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Guest house in Harpswell
The Bird House
2 bedrooms, 2 beds, 1 bathroom
21–26 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
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, 39 reviews
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Top guest favourite
Flat in Portland
Old Port Penthouse Suite - Amazing Harbor Views
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 327 reviews