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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Charming Modern West End Gem
2 bedrooms, 2 beds, 1 private bathroom
8–13 Nov
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4.93 out of 5 average rating, 325 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
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
3–8 Oct
4.96 out of 5 average rating, 57 reviews
Guest favourite
Flat in Portland
Clean and Bright, Two Blocks to the Prom!
3 bedrooms, 3 queen beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 280 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 18 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, 206 reviews
Top guest favourite
Home in Portland
East End Unit
1 bedroom, 2 beds, 1 bathroom
7–12 Nov
4.94 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 154 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, 486 reviews
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 74 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
Top guest favourite
Flat in South Portland
Stylish New Apartment Near Willard Beach w/ Yard
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 85 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
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.98 out of 5 average rating, 88 reviews
Guest favourite
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 5 reviews
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, 1250 reviews
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, 177 reviews