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Search results; Over 1,000 homes in Portland

Top guest favourite
Apartment in Portland
Top Of The Line Stay!
2 bedrooms, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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4.95 out of 5 average rating, 145 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds
13–18 Sept
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds
8–14 Nov
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 67 reviews
Cottage in Portland
Cozy Renovated Home | Portland, ME
2 bedrooms, 2 beds
1–6 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Barn in Portland
Garrison Cove Studio
1 bed
5–10 Nov
5.0 out of 5 average rating, 495 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, 223 reviews
Top guest favourite
Loft in Portland
Downtown Penthouse Suite - Stunning Harbor Views
2 bedrooms, 2 queen beds
25–30 Oct
4.97 out of 5 average rating, 322 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 153 reviews
Top guest favourite
Flat in Portland
PortJoy Living
2 bedrooms, 2 queen beds
26–31 Oct
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Portland
Captain Axel's Sophisticated Ocean View Getaway!
1 bedroom, 1 queen bed
23–28 Oct
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Home in Portland
Easy Old Port Access & Casco Bay View Craftsman
6 bedrooms, 10 beds
26–31 Oct
4.97 out of 5 average rating, 264 reviews
Top guest favourite
Flat in Portland
Amazing Views! Perfect Location. Loft style feel.
1 bedroom, 1 king bed
6–11 Nov
4.98 out of 5 average rating, 654 reviews
Top guest favourite
Flat in Portland
Stylish Condo in Downtown Portland w/ Private Yard
1 bedroom, 1 queen bed
25–30 Oct
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms, 10 beds
27 Sept – 2 Oct
4.88 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Portland
Luxury Retreat In Back Cove | 10 Min to Downtown
2 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 113 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, 154 reviews
Guest favourite
Flat in Portland
Old Port Loft - 301
2 bedrooms, 2 king beds
20–25 Sept
4.91 out of 5 average rating, 64 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 5 reviews