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Search results; Over 1,000 homes in Portland

Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 private bathroom
20–25 Sept
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5.0 out of 5 average rating, 74 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
Top guest favourite
Home in Portland
Modern Portland House - Minutes to the Old Port!
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 16 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, 24 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, 205 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 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
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
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
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds
20–25 Oct
4.96 out of 5 average rating, 375 reviews
Guest favourite
Flat in Portland
1875 West End Victorian | EV Charging + Parking
2 bedrooms, 3 beds
9–14 Nov
4.81 out of 5 average rating, 738 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
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 88 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
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 154 reviews
Guest favourite
Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms, 10 beds
27 Sept – 2 Oct
4.88 out of 5 average rating, 118 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
Guest favourite
Home in Portland
Stunning Ocean Views From This Peaks Island Home
3 bedrooms, 5 beds
27 Oct – 1 Nov
4.9 out of 5 average rating, 123 reviews
Guest favourite
Guest suite in Portland
Large, spacious, and eclectic Room, Private Bath
1 bedroom, 1 queen bed
26–31 Oct
4.89 out of 5 average rating, 759 reviews