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Search results; Over 1,000 homes in Portland

Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 private bathrooms
12–17 Oct
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4.96 out of 5 average rating, 178 reviews
Top 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
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
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
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
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
Guest favourite
Flat in Portland
1-bedroom unit (3 beds) with free parking
1 bedroom, 3 beds
1–6 Nov
4.95 out of 5 average rating, 151 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
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
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
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
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
Top guest favourite
Flat in Portland
Sophisticated Charm at an unbeatable price!
2 bedrooms, 2 beds
9–14 Nov
4.92 out of 5 average rating, 655 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Dec
4.98 out of 5 average rating, 89 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, 90 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, 224 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
Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds
20–25 Oct
4.95 out of 5 average rating, 376 reviews