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Search results; Over 1,000 homes in Portland

Guest favourite
Apartment in Portland
Historic West End Condo 10 Minute Walk to Old Port
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.93 out of 5 average rating, 153 reviews
Top guest favourite
Home in Portland
Modern Portland House - Minutes to the Old Port!
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds
9–14 Sept
5.0 out of 5 average rating, 17 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
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, 74 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds
7–12 Nov
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds
12–17 Oct
4.97 out of 5 average rating, 175 reviews
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Hotel room in Portland
Two Bedroom Loft featuring Curated Local Art
2 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 81 reviews
Guest favourite
Hotel room in Portland
Steps to Old Port | Hostel Bed in 8-Bed Coed Dorm
1 bedroom, 4 bunk beds
13–18 Sept
4.92 out of 5 average rating, 229 reviews
Top guest favourite
Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 88 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
Top guest favourite
Flat in Portland
Boutique BnB in The Heart of East End Portland!
2 bedrooms, 3 beds
30 Oct – 4 Nov
4.98 out of 5 average rating, 483 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
Top guest favourite
Flat in Portland
Central-Local Studio in Vibrant Portland, Maine!
1 bedroom, 1 queen bed
21–26 Dec
4.9 out of 5 average rating, 468 reviews
Top guest favourite
Home in Windham
Lakehouse on Highland Lake
4 bedrooms, 8 beds
26–31 Oct
4.97 out of 5 average rating, 89 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, 223 reviews
Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds
22–27 Oct
4.99 out of 5 average rating, 229 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, 302 reviews