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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.96 out of 5 average rating, 56 reviews
Home in Cape Elizabeth
Crescent Meadows
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
New place to stay
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
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
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 174 reviews
Guest favourite
Home in Portland
Historic Carriage House just steps from Casco Bay!
1 bedroom, 1 king bed, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 6 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
Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms, 4 beds, 2 bathrooms
30 Nov – 5 Dec
4.97 out of 5 average rating, 301 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, 186 reviews
Top guest favourite
Guest suite in Portland
Sunset Suite 42
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 238 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, 84 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
5.0 out of 5 average rating, 152 reviews
Top guest favourite
Flat in Portland
Glorious Getaway on the Eastern Promenade
2 bedrooms, 5 beds, 1 bathroom
18–23 Oct
4.93 out of 5 average rating, 650 reviews
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, 148 reviews
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 34 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
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 88 reviews
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, 16 reviews