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Search results; Over 1,000 homes in Portland

Guest favourite
Flat in Portland
Cozy West End Victorian | EV Charging + Parking
2 bedrooms, 2 beds, 1 private bathroom
8–13 Nov
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4.86 out of 5 average rating, 517 reviews
Superhost
Room in South Portland
HomeAwhile - Extended Stay Suites
2 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 177 reviews
Top guest favourite
Flat in Portland
Old Port Penthouse Suite - Amazing Harbor Views
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 325 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
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, 26 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
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
Large Sunny Apartment Near Downtown/Arts District
1 bedroom, 1 queen bed, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 481 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, 82 reviews
Top guest favourite
Home in Old Orchard Beach
Luxury Home w/HOT TUB & Fire Pit
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 228 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
Flat in Portland
Rooftop Deck | 5 Min to Downtown | Parking
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 72 reviews
Boat in Portland
Stay Aboard Enchanted – Your Dockside Getaway
2 bedrooms, 1 single bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Falmouth
Garden Guesthouse in Falmouth, 5 mins to Portland
1 bedroom, 2 king beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 366 reviews
Top guest favourite
Home in Saco
Oceanfront Escape • Walk to Beach • Sleeps 14
4 bedrooms, 11 beds, 3.5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Portland
West End Bright Spot with Parking.
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Portland
Sophisticated Charm at an unbeatable price!
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 646 reviews