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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
Modern Portland House - Minutes to the Old Port!
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 175 reviews
Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms, 5 beds, 1.5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 204 reviews
Top guest favourite
Flat in Portland
1-bedroom unit (3 beds) with free parking
1 bedroom, 3 beds, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 149 reviews
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
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, 223 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
20–25 Oct
4.96 out of 5 average rating, 374 reviews
Top guest favourite
Flat in Portland
Boutique BnB in The Heart of East End Portland!
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.98 out of 5 average rating, 482 reviews
Home in Cape Elizabeth
Crescent Meadows
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Portland
1875 West End Victorian | EV Charging + Parking
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
4.81 out of 5 average rating, 737 reviews
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Portland
Stunning Ocean Views From This Peaks Island Home
3 bedrooms, 5 beds, 2 bathrooms
27 Oct – 1 Nov
4.9 out of 5 average rating, 123 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
1 bedroom, 2 beds, 1 bathroom
22–27 Oct
4.99 out of 5 average rating, 229 reviews
Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Portland
Sunny 2-bedroom in Portland, ME
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 89 reviews