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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Chic Portland Penthouse, 2BR
2 bedrooms, 2 beds, 1 private bathroom
25–30 Oct
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4.98 out of 5 average rating, 156 reviews
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
Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms, 5 beds
20–25 Sept
4.86 out of 5 average rating, 206 reviews
Superhost
Hotel room in Portland
Steps to Old Port | Hostel Bed in 8-Bed Coed Dorm
1 bedroom, 4 bunk beds
15–20 Sept
4.92 out of 5 average rating, 229 reviews
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
Guest favourite
Flat in Portland
Clean and Bright, Two Blocks to the Prom!
3 bedrooms, 3 queen beds
25–30 Oct
4.89 out of 5 average rating, 280 reviews
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds
19–24 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds
16–21 Oct
5.0 out of 5 average rating, 18 reviews
Cottage in Portland
Cozy Renovated Home | Portland, ME
2 bedrooms, 2 beds
1–6 Nov
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds
25–30 Oct
4.92 out of 5 average rating, 304 reviews
Superhost
Rooms in Portland
Two Historic Downtown King Rooms w/Private Bath
2 bedrooms, 2 king beds
25–30 Oct
New place to stay
Top guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 155 reviews
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
Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds
20–25 Sept
4.95 out of 5 average rating, 42 reviews
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, 225 reviews
Top guest favourite
Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms, 4 beds
30 Nov – 5 Dec
4.97 out of 5 average rating, 304 reviews
Top guest favourite
Flat in South Portland
Stylish New Apartment Near Willard Beach w/ Yard
4 bedrooms, 5 beds
20–25 Sept
4.99 out of 5 average rating, 85 reviews
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 35 reviews