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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Historic Home in the West End. Private Parking.
1 bedroom, 2 beds, 2 private bathrooms
1–6 Nov
,
4.94 out of 5 average rating, 694 reviews
Superhost
Room in South Portland
HomeAwhile - Extended Stay Suites
2 beds, 1 bathroom
20–25 Aug
4.91 out of 5 average rating, 177 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Portland
Historic Carriage House just steps from Casco Bay!
1 bedroom, 1 king bed, 2 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Portland
Old Port Loft - 302
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 54 reviews
Home in Westbrook
Cozy Cape in the Brook
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Portland
Modern Studio Loft w/ Parking in Perfect Location
1 queen bed, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 779 reviews
Top guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
1 bedroom, 1 double bed, 1.5 bathrooms
1–6 Dec
4.95 out of 5 average rating, 556 reviews
Guest favourite
Guest suite in Portland
Large, spacious, and eclectic Room, Private Bath
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.89 out of 5 average rating, 749 reviews
Top guest favourite
Room in Biddeford
King Bedroom at Thistle Pond. Close to UNE & Beach
1 king bed, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 73 reviews
Top guest favourite
Guest house in Portland
Spacious & Convenient 2 Bd/1 bath w/ Free Parking
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 520 reviews
Guest favourite
Cabin in Freeport
22-ft dome w/ stargazing loft and full bath - 08
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
4.97 out of 5 average rating, 294 reviews
Top guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Portland
The Yankee Dugout
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 201 reviews
Top guest favourite
Flat in Biddeford
Modern Artist’s Loft
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 48 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, 145 reviews