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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
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
Top guest favourite
Home in Portland
Modern Portland House - Minutes to the Old Port!
3 bedrooms, 3 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 16 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
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, 26 reviews
Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
12–17 Oct
4.97 out of 5 average rating, 175 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 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
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, 483 reviews
Top guest favourite
Flat in Portland
Charming Modern West End Gem
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.93 out of 5 average rating, 323 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
Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 88 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, 205 reviews
Top guest favourite
Home in Portland
Waterfront-Beach Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 86 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
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, 8 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 40 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
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