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Search results; Over 1,000 homes in Portland

Guest favourite
Apartment in Portland
Historic West End Condo 10 Minute Walk to Old Port
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.93 out of 5 average rating, 153 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
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
Home in Cape Elizabeth
Crescent Meadows
3 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Hotel room in Portland
Steps to Old Port | Hostel Bed in 8-Bed Coed Dorm
1 bedroom, 4 bunk beds, 3.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 229 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 18 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, 57 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
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
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
4.98 out of 5 average rating, 88 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, 485 reviews
Top 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, 9 reviews
Guest favourite
Hotel room in Portland
Two Bedroom Loft featuring Curated Local Art
2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 81 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
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 Portland
FABULOUS! Working waterfront views. 94 walk score.
6 bedrooms, 8 beds, 4 bathrooms
22–27 Oct
4.96 out of 5 average rating, 156 reviews
Guest favourite
Flat in Portland
Workspace | Soaking Tub | W/D | 5 Min Downtown
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.92 out of 5 average rating, 24 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, 189 reviews
Guest favourite
Home in Portland
Little Island Cottage
3 bedrooms, 3 beds, 1 bathroom
10–15 Sept
4.97 out of 5 average rating, 35 reviews